Category: 4064-06-6

Singh, Yashapal; Demchenko, Alexei V. published the artcile< Koenigs-Knorr Glycosylation Reaction Catalyzed by Trimethylsilyl Trifluoromethanesulfonate>, Electric Literature of 4064-06-6, the main research area is oligosaccharide preparation Koenigs Knorr glycosylation trimethylsilyl trifluoromethanesulfonate catalyst; Koenigs-Knorr reaction; carbohydrates; glycosidation; synthetic methods.

The discovery that traditional silver(I)-oxide-promoted glycosidations of glycosyl bromides (Koenigs-Knorr reaction) can be greatly accelerated in the presence of catalytic trimethylsilyl trifluoromethanesulfonate (TMSOTf) is reported. The reaction conditions are very mild that allowed for maintaining a practically neutral pH and, at the same time, providing high rates and excellent glycosylation yields. In addition, unusual reactivity trends among a series of differentially protected glycosyl bromides were documented. In particular, benzoylated α-bromides were much more reactive than their benzylated counterparts under these conditions.

Chemistry – A European Journal published new progress about Cooperative phenomena (catalysis). 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Electric Literature of 4064-06-6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Brummel, Beau R.; Lee, Kinsey G.; McMillen, Colin D.; Kolis, Joseph W.; Whitehead, Daniel C. published the artcile< One-Pot Absolute Stereochemical Identification of Alcohols via Guanidinium Sulfate Crystallization>, Recommanded Product: ((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-5-yl)methanol, the main research area is alc absolute configuration one pot determination guanidinium sulfate crystallization.

A novel technique for the absolute stereochem. determination of alcs. has been developed that uses crystallization of guanidinium salts of organosulfates. The simple one-pot, two-step process leverages facile formation of guanidinium organosulfate single crystals for the straightforward determination of the absolute stereochem. of enantiopure alcs. by means of X-ray crystallog. The strong hydrogen bonding network drives the stability of the crystal lattice and allows for a diverse range of organic alc. substrates to be analyzed.

Organic Letters published new progress about Absolute configuration. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Recommanded Product: ((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-5-yl)methanol.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Bera, Srikrishna; Hu, Xile published the artcile< Nickel-Catalyzed Regioselective Hydroalkylation and Hydroarylation of Alkenyl Boronic Esters>, Recommanded Product: ((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-5-yl)methanol, the main research area is nickel catalyzed alkylation hydroarylation alkenyl boronic ester; aryl alkyl halide nickel catalyzed alkylation hydroarylation; alkenes; boron compounds; hydroalkylation; hydroarylation; nickel hydrides.

Metal hydride catalyzed hydrocarbonation reactions of alkenes are an efficient approach to construct new C-C bonds from readily available alkenes. However, the regioselectivity of hydrocarbonation remains challenging to be controlled. In Ni hydride (NiH) catalyzed hydrocarbonation, linear selectivity is most often obtained because of the relative stability of the linear Ni-alkyl intermediate over its branched counterpart. Herein, the boronic pinacol ester (Bpin) group directs a Ni-catalyzed hydrocarbonation to occur at its adjacent C center, resulting in formal branch selectivity. Both alkyl and aryl halides can be used as electrophiles in this hydrocarbonation, providing access to a wide range of secondary alkyl Bpin derivatives, which are valuable building blocks in synthetic chem. The utility of the method is demonstrated by the late-stage functionalization of natural products and drug mols., the synthesis of an anticancer agent, and iterative syntheses.

Angewandte Chemie, International Edition published new progress about Alkenes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (alkenylboranes). 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Recommanded Product: ((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-5-yl)methanol.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Keith, D. Jamin; Townsend, Steven D. published the artcile< Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit>, Reference of 4064-06-6, the main research area is zwitterionic polysaccharide immune response phosphoglycerol phosphocholine oligosaccharide; oligosaccharide Morganella Morganii trisaccharide repeating unit Zwitterionic phosphorylated glycosylation.

Zwitterionic polysaccharides (ZPS) activate T-cell-dependent immune responses by major histocompatibility complex class II presentation. Herein, we report the first synthesis of a Morganella morganii ZPS repeating unit as an enabling tool in the synthesis of novel ZPS materials. The repeating unit incorporates a 1,2-cis-α-glycosidic bond; the problematic 1,2-trans-galactosidic bond, Gal-β(1→3)-GalNAc; and phosphoglycerol and phosphocholine residues which have not been previously observed together as functional groups on the same oligosaccharide. The successful third generation approach leverages a first in class glycosylation of a phosphoglycerol functionalized acceptor. To install the phosphocholine unit, a highly effective phosphocholine donor was synthesized.

Journal of the American Chemical Society published new progress about Glycosylation. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Reference of 4064-06-6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Rushworth, James L.; Montgomery, Katherine S.; Cao, Benjamin; Brown, Robert; Dibb, Nick J.; Nilsson, Susan K.; Chiefari, John; Fuchter, Matthew J. published the artcile< Glycosylated Nanoparticles Derived from RAFT Polymerization for Effective Drug Delivery to Macrophages>, Synthetic Route of 4064-06-6, the main research area is macrophage targeting drug carrier polymer; CD206; drug delivery; glycopolymers; macrophages; mannose; tumor-associated macrophages.

The functional group tolerance and simplicity of reversible addition fragmentation chain transfer (RAFT) polymerization enable its use in the preparation of a wide range of functional polymer architectures for a variety of applications, including drug delivery. Given the role of tumor-associated macrophages (TAMs) in cancer and their dependence on the tyrosine kinase receptor FMS (CSF-1R), the key aim of this work was to achieve effective delivery of an FMS inhibitor to cells using a polymer delivery system. Such a system has the potential to exploit biol. features specific to macrophages and therefore provide enhanced selectivity. Building on our prior work, we have prepared RAFT polymers based on a poly(Bu methacrylate-co-methacrylic acid) diblock, which were extended with a hydrophilic block, a cross-linker, and a mannose-based monomer scaffold, exploiting the abundance of macrophage mannose receptors (MMRs, CD206) on the surface of macrophages. We demonstrate that the prepared polymers can be assembled into nanoparticles and are successfully internalized into macrophages, in part, via the MMR (CD206). Finally, we showcase the developed nanoparticles in the delivery of an FMS inhibitor to cells, resulting in inhibition of the FMS receptor. As such, this study lays the groundwork for further drug-delivery studies aimed at specifically targeting TAMs with molecularly targeted therapeutics.

ACS Applied Bio Materials published new progress about Biological uptake. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Synthetic Route of 4064-06-6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Ferreira, Joana T.; Pina, Joao; Ribeiro, Carlos A. F.; Fernandes, Rosa; Tome, Joao P. C.; Rodriguez-Morgade, M. Salome; Torres, Tomas published the artcile< Highly Efficient Singlet Oxygen Generators Based on Ruthenium Phthalocyanines: Synthesis, Characterization and in vitro Evaluation for Photodynamic Therapy>, Quality Control of 4064-06-6, the main research area is glucose galactose mannose ruthenium phthalocyanine preparation photodynamic therapy; carbohydrates; photodynamic therapy; phthalocyanines; ruthenium; singlet oxygen.

The synthesis of ruthenium(II) phthalocyanines (RuPcs) endowed with one carbohydrate unit-i.e., glucose, galactose and mannose-and a dimethylsulfoxide (DMSO) ligand at the two axial coordination sites, resp., is described. Two series of compounds, one unsubstituted at the periphery, and the other one bearing eight PEG chains at the isoindole meta-positions, have been prepared The presence of the axial DMSO unit significantly increases the phthalocyanine singlet oxygen quantum yields, related to other comparable RuPcs. The compounds have been evaluated for PDT treatment in bladder cancer cells. In vitro studies have revealed high phototoxicity for RuPcs unsubstituted at their periphery. The phototoxicity of PEG-substituted RuPcs has been considerably improved by repeated light irradiation The choice of the axial carbohydrate introduced little differences in the cellular uptake for both series of photosensitizers, but the phototoxic effects were considerably higher for compounds bearing mannose units.

Chemistry – A European Journal published new progress about Bladder neoplasm. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Quality Control of 4064-06-6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Isilar, Ozer; Bulut, Adnan; Sahin Yaglioglu, Ayse; Demirtas, Ibrahim; Arat, Esra; Turk, Mustafa published the artcile< Synthesis and biological evaluation of novel urea, thiourea and squaramide diastereomers possessing sugar backbone>, Formula: C12H20O6, the main research area is antiproliferative antitumor aminoglycoside disaccharide preparation; aminoglycoside disaccharide preparation urea thiourea squaramide human; Antiproliferative activity; Cytotoxicity; Squaramide; Sugar; Thiourea; Urea.

A series of novel chiral 14 urea, thiourea and squaramide stereoisomers possessing carbohydrate backbones as well as amide functional groups was synthesized and characterized by their, 1H NMR, 13C NMR, FT-IR, HRMS, optical rotation, and m.ps. Their antiproliferative activities were investigated against HeLa and PC3 cell lines. Aminoglycosides I (X = S, O) showed better activities at 25μM against PC3 cell line with respect to the standard 5-fluorouracil (5-FU). Especially, the compounds 9 and 11 showed higher activities than the standard 5-FU even at low concentration (5μM) against HeLa cell line. IC50 results also confirm these activities. The compounds I (X = S, O) have the IC50 values of 1.10μM and 1.02μM, resp. while 5-FU has 2.51μM.

Carbohydrate Research published new progress about Aminoglycosides Role: PAC (Pharmacological Activity), RCT (Reactant), SPN (Synthetic Preparation), THU (Therapeutic Use), BIOL (Biological Study), RACT (Reactant or Reagent), PREP (Preparation), USES (Uses). 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Formula: C12H20O6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Santana, Andres G.; Montalvillo-Jimenez, Laura; Diaz-Casado, Laura; Mann, Enrique; Jimenez-Barbero, Jesus; Gomez, Ana M.; Asensio, Juan Luis published the artcile< Single-Step Glycosylations with 13C-Labelled Sulfoxide Donors: A Low-Temperature NMR Cartography of the Distinguishing Mechanistic Intermediates>, Related Products of 4064-06-6, the main research area is NMR glycosylation cartog glycosyl sulfoxide donor intermediate detection monitoring; NMR spectroscopy; carbohydrates; glycosylation; isotopic labelling; reaction mechanisms.

Glycosyl sulfoxides have gained recognition in the total synthesis of complex oligosaccharides and as model substrates for dissecting the mechanisms involved. Reactions of these donors are usually performed under pre-activation conditions, but an exptl. more convenient single-step protocol has also been reported, whereby activation is performed in the presence of the acceptor alc.; yet, the nature and prevalence of the reaction intermediates formed in this more complex scenario have comparatively received minimal attention. Herein, a systematic NMR-based study employing both 13C-labeled and unlabeled glycosyl sulfoxide donors for the detection and monitoring of marginally populated intermediates is reported. The results conclusively show that glycosyl triflates play a key role in these glycosylations despite the presence of the acceptor alc. Importantly, the formation of covalent donor/acceptor sulfonium adducts was identified as the main competing reaction, and thus a non-productive consumption of the acceptor that could limit the reaction yield was revealed.

Chemistry – A European Journal published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Related Products of 4064-06-6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Isilar, Ozer; Bulut, Adnan; Sahin Yaglioglu, Ayse; Demirtas, Ibrahim; Arat, Esra; Turk, Mustafa published the artcile< Synthesis and biological evaluation of novel urea, thiourea and squaramide diastereomers possessing sugar backbone>, Formula: C12H20O6, the main research area is antiproliferative antitumor aminoglycoside disaccharide preparation; aminoglycoside disaccharide preparation urea thiourea squaramide human; Antiproliferative activity; Cytotoxicity; Squaramide; Sugar; Thiourea; Urea.

A series of novel chiral 14 urea, thiourea and squaramide stereoisomers possessing carbohydrate backbones as well as amide functional groups was synthesized and characterized by their, 1H NMR, 13C NMR, FT-IR, HRMS, optical rotation, and m.ps. Their antiproliferative activities were investigated against HeLa and PC3 cell lines. Aminoglycosides I (X = S, O) showed better activities at 25μM against PC3 cell line with respect to the standard 5-fluorouracil (5-FU). Especially, the compounds 9 and 11 showed higher activities than the standard 5-FU even at low concentration (5μM) against HeLa cell line. IC50 results also confirm these activities. The compounds I (X = S, O) have the IC50 values of 1.10μM and 1.02μM, resp. while 5-FU has 2.51μM.

Carbohydrate Research published new progress about Aminoglycosides Role: PAC (Pharmacological Activity), RCT (Reactant), SPN (Synthetic Preparation), THU (Therapeutic Use), BIOL (Biological Study), RACT (Reactant or Reagent), PREP (Preparation), USES (Uses). 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Formula: C12H20O6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Santana, Andres G.; Montalvillo-Jimenez, Laura; Diaz-Casado, Laura; Mann, Enrique; Jimenez-Barbero, Jesus; Gomez, Ana M.; Asensio, Juan Luis published the artcile< Single-Step Glycosylations with 13C-Labelled Sulfoxide Donors: A Low-Temperature NMR Cartography of the Distinguishing Mechanistic Intermediates>, Related Products of 4064-06-6, the main research area is NMR glycosylation cartog glycosyl sulfoxide donor intermediate detection monitoring; NMR spectroscopy; carbohydrates; glycosylation; isotopic labelling; reaction mechanisms.

Glycosyl sulfoxides have gained recognition in the total synthesis of complex oligosaccharides and as model substrates for dissecting the mechanisms involved. Reactions of these donors are usually performed under pre-activation conditions, but an exptl. more convenient single-step protocol has also been reported, whereby activation is performed in the presence of the acceptor alc.; yet, the nature and prevalence of the reaction intermediates formed in this more complex scenario have comparatively received minimal attention. Herein, a systematic NMR-based study employing both 13C-labeled and unlabeled glycosyl sulfoxide donors for the detection and monitoring of marginally populated intermediates is reported. The results conclusively show that glycosyl triflates play a key role in these glycosylations despite the presence of the acceptor alc. Importantly, the formation of covalent donor/acceptor sulfonium adducts was identified as the main competing reaction, and thus a non-productive consumption of the acceptor that could limit the reaction yield was revealed.

Chemistry – A European Journal published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Related Products of 4064-06-6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts