Category: 85618-21-9

Ueda, Yoshihiro published the artcileFunctional Group Tolerance in Organo-Catalytic Regioselective Acylation of Carbohydrates, SDS of cas: 85618-21-9, the publication is Journal of Organic Chemistry (2009), 74(22), 8802-8805, database is CAplus and MEDLINE.

Organo-catalytic regioselective acylation of mono- and disaccharides with various functionalized acid anhydrides has been developed. Acylation of octyl β-D-glucopyranoside with acid anhydrides derived from α-amino acids, cinnamic acid, and gallic acid took place at C(4)-OH with 67-94% regioselectivity in the presence of catalyst I. Regioselective acylation of disaccharides with functionalized acid anhydrides was also achieved with 78-94% selectivity. Especially, a disaccharide with seven free hydroxy groups (X = OH, R’ = H) underwent acylation at C(4)-OH with 78% regioselectivity in the presence of I. Thus, functional group tolerance in the regioselective acylation catalyzed by I was found to be high.

Journal of Organic Chemistry published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C9H6BrNO, SDS of cas: 85618-21-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Kawabata, Takeo published the artcileA Catalytic One-Step Process for the Chemo- and Regioselective Acylation of Monosaccharides, SDS of cas: 85618-21-9, the publication is Journal of the American Chemical Society (2007), 129(42), 12890-12895, database is CAplus and MEDLINE.

An organo-catalytic method for the chemo- and regioselective acylation of monosaccharides has been developed. Treatment of octyl β-D-glucopyranoside with isobutyric anhydride in the presence of 10 mol % of a C₂-sym. chiral 4-pyrrolidinopyridine catalyst at -50 °C gave the 4-O-isobutyryl derivative as the sole product in 98% yield. Thus, chemoselective acylation, favoring a secondary hydroxyl group in the presence of a free primary hydroxyl group, and regioselective acylation, favoring one of three secondary hydroxyl groups, took place with perfect selectivity. A competitive acylation between octyl β-D-glucopyranoside and a primary alc. (2-phenylethanol) with 1.1 equiv of isobutyric anhydride in the presence of 4-pyrrolidinopyridine catalyst gave the 4-O-isobutyrate of octyl β-D-glucopyranoside with 99% regioselectivity in 98% yield, which indicates that acylation of the secondary hydroxyl group at C(4) of the carbohydrate proceeds in an accelerative manner. A possible mechanism, involving multiple hydrogen-bonding between 4-pyrrolidinopyridine catalyst and the monosaccharide, is proposed for the chemo- and regioselective acylation.

Journal of the American Chemical Society published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C14H28O5S, SDS of cas: 85618-21-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Tarif, Ejaj published the artcileDynamics at the non-ionic micelle/water interface: Impact of linkage substitution, Related Products of alcohols-buliding-blocks, the publication is Journal of Chemical Physics (2019), 151(15), 154902/1-154902/9, database is CAplus and MEDLINE.

The impact of atom substitution on the glycoside linkage bridging the head and the tail parts in a nonionic surfactant mol. on aqueous dynamics of the resultant micellar solutions has been explored, employing time-resolved fluorescence and dielec. relaxation (DR) measurements. We have utilized n-octyl-β-D-glucopyranoside (OG) and n-octyl-β-D-thioglucopyranoside (OTG) as nonionic surfactants where the oxygen atom in the glucopyranoside unit is substituted by a sulfur atom. The substitution impact is immediately reflected in the dynamic light scattering measurements of aqueous solutions where the estimated size of the OTG micelles is found to be approx. four times larger than the OG micelles. Steady state spectral features obtained by using a fluorescent probe solute, coumarin 153 (C153), in these micellar solutions are quite similar and indicate locations of the solute at the micelle/water interface for both the surfactants. Interestingly, significant differences in the rotational and solvation dynamics of C153 in these two micellar solutions have been registered. The corresponding DR measurements do not indicate any signature of relaxation typical of bound water. The absence of bound water is further supported by the differential scanning calorimetric measurements. However, the typical slow solvation time scale for aqueous micellar solutions has been observed for these surfactants. Fluctuations in the solute-interface interaction energy due to the solute motion has been argued to be the origin for this slow solvation component as DR measurements do not indicate the presence of qual. similar relaxation time scale in the medium. (c) 2019 American Institute of Physics.

Journal of Chemical Physics published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C6H8O3, Related Products of alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Ruiz, Cristobal Carnero published the artcileSelf-assembly, surface activity and structure of n-octyl-β-D-thioglucopyranoside in ethylene glycol-water mixtures, SDS of cas: 85618-21-9, the publication is International Journal of Molecular Sciences (2013), 3228-3253, database is CAplus and MEDLINE.

The effect of the addition of ethylene glycol (EG) on the interfacial adsorption and micellar properties of the alkylglucoside surfactant n-octyl-β-D-thioglucopyranoside (OTG) has been investigated. Critical micelle concentrations (cmc) upon EG addition were obtained by both surface tension measurements and the pyrene 1:3 ratio method. A systematic increase in the CMC induced by the presence of the co-solvent was observed This behavior was attributed to a reduction in the cohesive energy of the mixed solvent with respect to pure water, which favors an increase in the solubility of the surfactant with EG content. Static light scattering measurements revealed a decrease in the mean aggregation number of the OTG micelles with EG addition Moreover, dynamic light scattering data showed that the effect of the surfactant concentration on micellar size is also controlled by the content of the co-solvent in the system. Finally, the effect of EG addition on the microstructure of OTG micelles was investigated using the hydrophobic probe Coumarin 153 (C153). Time-resolved fluorescence anisotropy decay curves of the probe solubilized in micelles were analyzed using the two-step model. The results indicate a slight reduction of the average reorientation time of the probe mol. with increasing EG in the mixed solvent system, thereby suggesting a lesser compactness induced by the presence of the co-solvent.

International Journal of Molecular Sciences published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C14H28O5S, SDS of cas: 85618-21-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Hierrezuelo, J. M. published the artcileOn the Urea Action Mechanism: A Comparative Study on the Self-Assembly of Two Sugar-Based Surfactants, Synthetic Route of 85618-21-9, the publication is Journal of Physical Chemistry B (2009), 113(20), 7178-7187, database is CAplus and MEDLINE.

Studies on the effect of urea on micelle formation and structure of n-octyl-β-D-thioglucoside (OTG) and N-decanoyl-N-methylglucamide (MEGA-10) were carried out by using the steady-state and time-resolved fluorescence techniques, together with combined static and dynamic light scattering measurements. A similar increase in the critical micelle concentration with the urea addition was observed for both surfactants. This behavior was attributed to a rise in the solubility of hydrocarbon tails and the increase of solvation of the headgroup of the surfactants in the presence of urea. Structural studies mainly based on the anal. of the hydrodynamic radius and aggregation number of micelles revealed that urea induces changes much more significant on micelles of OTG. Particularly, it was found that, whereas the surface area per headgroup of OTG increases with the urea concentration, it does decrease in the case of MEGA-10. This fact suggests that different action mechanisms operate for both surfactants. Accordingly, investigations on the micellar microstructure based on the study of microenvironmental properties such as micropolarity and microviscosity also indicated a more pronounced effect in the case of OTG. Although changes were not observed in the hydrophobic inner region of both micellar systems, a significant increase of polarity and viscosity in the micellar interface of OTG suggests a direct participation of urea in the micellar solvation layer. The differences between the observed behaviors for both micellar systems were interpreted on the basis of two features: the weaker hydration and greater rigidity of the OTG headgroup as compared with MEGA-10.

Journal of Physical Chemistry B published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C14H28O5S, Synthetic Route of 85618-21-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Carnero Ruiz, C. published the artcileCharacterization of mixed nonionic surfactants n-octyl-β-D-thioglucoside and octaethylene-glycol monododecyl ether: Micellization and microstructure, Computed Properties of 85618-21-9, the publication is Journal of Colloid and Interface Science (2011), 361(1), 178-185, database is CAplus and MEDLINE.

Mixed micelles of n-octyl-β-D-thioglucoside (OTG) and octaethylene-glycol monododecyl ether (C₁₂E₈), two nonionic surfactants belonging to the alkyl glucosides and polyoxyethylene alkyl ether families, resp., were studied by using light scattering and fluorescence probe techniques. From the determination of the critical micelle concentration (cmc), by the well-established pyrene 1:3 ratio method, the mixed system behaves ideally, the micellization process being clearly controlled by the ethoxylated surfactant. The micellar hydrodynamic radius as a function of temperature, composition and concentration was obtained by dynamic light scattering measurements. The micellar size increases with temperature, this growth being more pronounced as the relative proportion of the ethoxylated surfactant was increased. The behavior of the micellar size with the total surfactant concentration also is dependent on temperature and composition The clouding temperature, characteristic of the ethoxylated surfactants, was increased with the addition of the sugar surfactant. Lastly, possible structural changes in the micellar palisade layer were examined by steady-state fluorescence anisotropy in conjunction with time-resolved fluorescence studies with the hydrophobic probe coumarin 6 (C6). The participation of the ethoxylated surfactant induces a slightly more polar palisade layer, whereas the probe carries out a faster rotational reorientation as a result of a less compact environment. All these observations were attributed to the different structure of the head groups of both surfactants and, as a consequence, to their different hydration.

Journal of Colloid and Interface Science published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C14H28O5S, Computed Properties of 85618-21-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Muramatsu, Wataru published the artcilePerfectly Regioselective and Sequential Protection of Glucopyranosides, SDS of cas: 85618-21-9, the publication is European Journal of Organic Chemistry (2010), 827-831, S827/1-S827/67, database is CAplus.

A perfectly regioselective and sequential method for the preparation of orthogonally protected glucopyranosides has been developed. An acyl group was introduced at C(4)-OH by organocatalysis with >99 % regioselectivity. TBDPS, Boc, and BOM groups were sequentially introduced into the 4-O-acyl-glucopyranoside at C(6)-OH, C(2)-OH, and C(3)-OH, resp., with ca. 100 % regioselectivity in each step.

European Journal of Organic Chemistry published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C14H28O5S, SDS of cas: 85618-21-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Raju, Rekha published the artcilen-Octyl (thio)glycosides as potential cryoprotectants: Glass transition behaviour, membrane permeability, and ice recrystallization inhibition studies, Recommanded Product: (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, the publication is Australian Journal of Chemistry (2019), 72(8), 637-643, database is CAplus.

A series of eight n-octyl (thio)glycosides (1α, β-4α, β) with d-glucose or d-galactose-configured head groups and varying anomeric configuration were synthesized and evaluated for glass transition behavior, membrane permeability, and ice recrystallization inhibition (IRI) activity. Of these, n-octyl β-d-glucopyranoside (2β) exhibited a high glass transition temperatures (Tg), both as a neat sample and 20 wt-% aqueous solution Membrane permeability studies of this compound revealed cellular uptake to concentrations relevant to the inhibition of intracellular ice formation, thus presenting a promising lead candidate for further biophys. and cryopreservation studies. Compounds were also evaluated as ice recrystallization inhibitors; however, no detectable activity was observed for the newly tested compounds

Australian Journal of Chemistry published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C14H28O5S, Recommanded Product: (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Tran, Chieu D. published the artcileChiral ionic liquids for enantioseparation of pharmaceutical products by capillary electrophoresis, Category: alcohols-buliding-blocks, the publication is Journal of Chromatography A (2008), 1204(2), 204-209, database is CAplus and MEDLINE.

A chiral ionic liquid (IL), S-[3-(chloro-2-hydroxypropyl)trimethylammonium] [bis((trifluoromethyl)sulfonyl)amide] (S-[CHTA]⁺[Tf₂N]^–), which can be easily and readily synthesized in a one-step process from com. available reagents, can be successfully used both as co-electrolyte and as a chiral selector for CE. A variety of pharmaceutical products including atenolol, propranolol, warfarin, indoprofen, ketoprofen, ibuprofen and flurbiprofen, can be successfully and baseline separated with the use of this IL as electrolyte. Interestingly, while S-[CHTA]⁺[Tf₂N]^– can also serve as a chiral selector, enantioseparation cannot be successfully achieved with S-[CHTA]⁺[Tf₂N]^– as the only chiral selector. In the case of ibuprofen, a second chiral selector, namely a chiral anion (sodium cholate), is needed for the chiral separation For flurbiprofen, in addition to S-[CHTA]⁺[Tf₂N]^– and sodium cholate, a third and neutral chiral selector, 1-S-octyl-β–thioglucopyranoside (OTG), is also needed. Due to the fact that the chirality of this chiral IL resides on the cation (i.e., -[CHTA]⁺), and that needed addnl. chiral selector(s) are either chiral anion (i.e., cholate) or chiral neutral compound (OTG), the results obtained seem to suggest that addnl. chiral selector(s) are needed to provide the three-point interactions needed for chiral separations

Journal of Chromatography A published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C3H5BN2O2, Category: alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Varade, Vaibhav published the artcileBacteriorhodopsin based non-magnetic spin filters for biomolecular spintronics, Safety of (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, the publication is Physical Chemistry Chemical Physics (2018), 20(2), 1091-1097, database is CAplus and MEDLINE.

We discuss spin injection and spin valves, which are based on organic and biomols., that offer the possibility to overcome some of the limitations of solid-state devices, which are based on ferromagnetic metal electrodes. In particular, we discuss spin filtering through bacteriorhodopsin in a solid state biomol. spin valve that is based on the chirality induced spin selectivity (CISS) effect and shows a magnetoresistance of ∼2% at room temperature The device is fabricated using a layer of bacteriorhodopsin (treated with n-octyl-thioglucoside detergent: OTG-bR) that is adsorbed on a cysteamine functionalized gold electrode and capped with a magnesium oxide layer as a tunneling barrier, upon which a Ni top electrode film is placed and used as a spin analyzer. The bR based spin valves show an antisym. magnetoresistance response when a magnetic field is applied along the direction of the current flow, whereas they display a pos. sym. magnetoresistance curve when a magnetic field is applied perpendicular to the current direction.

Physical Chemistry Chemical Physics published new progress about 85618-21-9. 85618-21-9 belongs to alcohols-buliding-blocks, auxiliary class Tetrahydropyran,Chiral,sulfides,Alcohol, name is (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C6H12O2, Safety of (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(octylthio)tetrahydro-2H-pyran-3,4,5-triol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts