Tag: M.W=200-250

Choutka, Jan published the artcileStraightforward synthesis of protected 2-hydroxyglycals by chlorination-dehydrochlorination of carbohydrate hemiacetals, Related Products of alcohols-buliding-blocks, the main research area is hydroxyglycal chlorination dehydrochlorination glycosyl chloride protecting group monosaccharide; 2-Hydroxyglycals; Carbohydrates; Dehydrochlorination; Glycals; Glycosyl chlorides.

A straightforward and scalable method for the synthesis of protected 2-hydroxyglycals is described. The approach is based on the chlorination of carbohydrate-derived hemiacetals, followed by an elimination reaction to establish the glycal moiety. 1,2-dehydrochlorination reactions were studied on a range of glycosyl chlorides to provide suitable reaction conditions for this transformation. Benzyl ether, isopropylidene and benzylidene protecting groups, as well as inter-glycosidic linkage, were found to be compatible with this protocol. The described method is operationally simple and allows for the quick preparation of 2-hydroxyglycals with other than ester protecting groups, providing a feasible alternative to existing methods.

Carbohydrate Research published new progress about Chlorination. 2595-07-5 belongs to class alcohols-buliding-blocks, name is (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C9H16O6, Related Products of alcohols-buliding-blocks.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Baldoneschi, Veronica published the artcileActive-Site Targeting Paramagnetic Probe for Matrix Metalloproteinases, Application In Synthesis of 87905-98-4, the main research area is ytterbium lanthanum complex paramagnetism active site matrix metalloproteinase MMP12; DOTA; inhibitors; lanthanides; metalloproteins; molecular probes.

The design and synthesis of the Ln3+ complexes of a DOTA-containing (DOTA = 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid) inhibitor of matrix metalloproteinases are reported. The tight binding of the sulfonamide scaffold to the catalytic domain of the investigated matrix metalloproteinase is not impaired by the presence of the Ln3+-DOTA moiety. The paramagnetic properties of the Ln3+ complex are exploited to obtain insights into the structural features of the ligand-protein interactions and to evaluate the influence of the linker length on the quality of the paramagnetic restraints.

ChemPlusChem published new progress about Complexation. 87905-98-4 belongs to class alcohols-buliding-blocks, name is Benzyl (5-hydroxypentyl)carbamate, and the molecular formula is C13H19NO3, Application In Synthesis of 87905-98-4.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Gerbst, Alexey G. published the artcileDriving Force of the Pyranoside-into-Furanoside Rearrangement, Formula: C9H16O6, the main research area is pyranoside furanoside rearrangement.

Ab initio calculations of fully O-sulfated model monosaccharides, including common hexoses (glucose, galactose, fucose, and mannose) and pentoses (arabinose and xylose), were performed to study the energetic properties of the recently discovered pyranoside-into-furanoside (PIF) rearrangement. It was shown that the per-O-sulfated derivatives of furanoside isomers generally had lower energies than the corresponding per-O-sulfated pyranosides, while nonsulfated furanosides were always less favored than nonsulfated pyranosides. Mannose, which is known to be unreactive in PIF rearrangement, was the only exception. The results of the theor. calculations were confirmed by exptl. studies of monosaccharide models and explained the driving force of such unusual ring contraction process as PIF rearrangement. The conclusions of performed investigation can be used for prediction of new substrates applicability for PIF rearrangement.

ACS Omega published new progress about Conformation. 2595-07-5 belongs to class alcohols-buliding-blocks, name is (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C9H16O6, Formula: C9H16O6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Barlow, Thomas published the artcileAralkylation of Guanosine with p-Substituted Styrene Oxides, Formula: C8H9BrO2, the main research area is aralkylation guanosine styrene oxide.

To probe mechanisms of nucleoside aralkylation, product distributions and product stereochemistries were determined in reactions of optically active p-methyl- and p-bromo-styrene oxide with guanosine. The proportion of 7-, N2- and O6-substituted guanosine products was 0.32:0.62:0.06 in neutral, aqueous reactions of the (R) p-methylstyrene oxide and 0.85:0.09:0.04 in reactions with the (R) p-bromostyrene oxide. The exocyclic positions opened The epoxide at the α-carbon. Epoxide ring-opening by the nitrogen at the 7-position showed little preference for the α- or β-carbons in reactions with p-methylstyrene oxide. However, the p-bromostyrene oxide favored reaction at the β-carbon almost 4-fold over reaction at the α-carbon. Almost total inversion of stereochem. was found to occur in reactions at the 7-position. In contrast, the ratio of inversion to retention of configuration in N- and O-substituted products was 2:1 and 1:1 for reactions with the p-methylstyrene oxide and 6:1 and 3:1 for reactions with p-bromostyrene oxide, resp. These experiments suggest that an SN2 mechanism is in effect with reactions at the 7-position, whereas substrates of an increasingly ionic nature are involved in reactions at the N2- and O6- positions, resp.

Chemical Research in Toxicology published new progress about Aralkylation. 92093-23-7 belongs to class alcohols-buliding-blocks, name is 1-(4-Bromophenyl)ethane-1,2-diol, and the molecular formula is C8H9BrO2, Formula: C8H9BrO2.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Kartha, Ravindranathan K. P. published the artcileSimple and efficient strategy for making β-(1→6)-linked galactooligosaccharides using ‘naked’ galactopyranosides as acceptors, Computed Properties of 2595-07-5, the main research area is galactooligosaccharide beta linked preparation; galactopyranoside unprotected regioselective stereoselective glycosidation acetobromosugar.

Unprotected (naked) galactopyranosides were used for the first time in the direct regio- and stereoselective synthesis of β-(1→6)-linked oligosaccharides in 75-90% yield by coupling them with acetobromosugars in the presence of silver carbonate in dichloromethane. β-(1→4)-Linked oligosaccharides (yield 5-10%) were the byproducts. Thus, glycoside I (OSE = OCH2CH2SiMe3)was reacted with bromide II in the presence of Ag2CO3 in CH2Cl2 to give the disaccharide III (R = H).

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry published new progress about Glycosylation. 2595-07-5 belongs to class alcohols-buliding-blocks, name is (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol, and the molecular formula is C9H16O6, Computed Properties of 2595-07-5.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Chatterjee, Manashi N. published the artcileBeyond Switches: Ratcheting a Particle Energetically Uphill with a Compartmentalized Molecular Machine, Formula: C13H19NO3, the main research area is switch particle energy uphill compartment mol machine.

Here we correlate chem. (covalent), phys. (thermodn.), and statistical (population distribution) descriptions of behavior with the way that two new types of simple mol. machines (the threads of rotaxanes) perform the task of transporting a Brownian substrate (the rotaxane macrocycle) between two distinguishable binding sites. The first machine-substrate ensemble is a [2]rotaxane that operates through a mechanism that intrinsically causes it to change the average position of the macrocycle irreversibly. This contrasts with the behavior of classic stimuli-responsive mol. shuttles that act as reversible mol. switches. The second system is a compartmentalized mol. machine that is able to pump its substrate energetically uphill using the energy provided by a photon by means of an olefin photoisomerization. Resetting this compartmentalized mol. machine does not undo the work it has carried out or the task performed, a significant difference to a simple mol. switch and a characteristic we recognize as “”ratcheting”” (see Scheme 8). The ratcheting mechanism allows the [2]rotaxane to carry out the transport function envisaged for the historical thought-machines, Smoluchowski’s Trapdoor and Maxwell’s Pressure Demon, albeit via an unrelated mechanism and using an input of energy. We define and exemplify the terms “”ratcheting”” and “”escapement”” in mech. terms for the mol. level and outline the fundamental phenomenol. differences that exist between what constitutes a two-state Brownian switch, a two-state Brownian memory or “”flip-flop””, and a (two-stroke) Brownian motor. We also suggest that considering the relationship between the parts of a mol. machine and a substrate in terms of “”statistical balance”” and “”linkage”” could be useful in the design of more complex systems and in helping to understand the role of individual amino acids and peptide fragments during the directional transport of substrates by biol. pumps and motors.

Journal of the American Chemical Society published new progress about Hydrogen bond. 87905-98-4 belongs to class alcohols-buliding-blocks, name is Benzyl (5-hydroxypentyl)carbamate, and the molecular formula is C13H19NO3, Formula: C13H19NO3.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Cipolla, Laura published the artcileGlycosyl sulfates as glycosyl donors, Quality Control of 87905-98-4, the main research area is glycosyl sulfate glycosidation; glycoside preparation glycosyl sulfate; disaccharide preparation glycosyl sulfate.

2,3,4,6-Tetra-O-benzyl-D-glucopyranose was treated with SO3.NMe3 complex to give 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl sulfate trimethylamine salt (α:β = 3:1), which when reacted with various acceptors promoted by Lewis acids gave glycosides and disaccharides as α,β mixtures For example, coupling 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl sulfate with 2,3,4,6-tetra-O-α-D-glucopyranose gave trehaloses in 96% overall yield (β,α:α,α:β,β = 8:4:3).

Tetrahedron Letters published new progress about Glycosylation. 87905-98-4 belongs to class alcohols-buliding-blocks, name is Benzyl (5-hydroxypentyl)carbamate, and the molecular formula is C13H19NO3, Quality Control of 87905-98-4.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Naresh, K. published the artcilePushing the limits of automated glycan assembly: synthesis of a 50mer polymannoside, Recommanded Product: Benzyl (5-hydroxypentyl)carbamate, the main research area is oligosaccharide mannooligosaccharide preparation polysaccharide automated glycan assembly glycosylation.

Automated glycan assembly (AGA) enables rapid access to oligosaccharides. The overall length of polymers created via automated solid phase synthesis depends on very high yields at every step to obtain full length products. The synthesis of long polymers serves as the ultimate test of the efficiency and reliability of synthetic processes. A series of Man-(1→6)-α-Man linked oligosaccharides up to a 50mer, the longest synthetic sequence yet assembled from monosaccharides, has been realized via a 102 step synthesis. We identified a suitable mannose building block and applied a capping step in the final five AGA cycles to minimize (n – 1) deletion sequences that are otherwise difficult to remove by HPLC.

Chemical Communications (Cambridge, United Kingdom) published new progress about Glycosylation. 87905-98-4 belongs to class alcohols-buliding-blocks, name is Benzyl (5-hydroxypentyl)carbamate, and the molecular formula is C13H19NO3, Recommanded Product: Benzyl (5-hydroxypentyl)carbamate.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Cerofolini, Linda published the artcileSynthesis and binding monitoring of a new nanomolar PAMAM-based matrix metalloproteinases inhibitor (MMPIs), Quality Control of 87905-98-4, the main research area is preparation PAMAM dendrimer matrix metalloproteinase inhibitor dry eye syndrome; Dendrimers; Inhibitors; Metalloproteins; NMR spectroscopy; Sulphonamidic scaffold.

Dendrimers are efficient drug delivery systems particularly useful in ocular diseases. In particular, low generation PAMAM dendrimers are non-toxic and non-immunogenic and they provide an enhancement of the residence time of drugs in the eyes. In this context, the synthesis of the PAMAM-based matrix metalloproteinases inhibitor 5, is reported. In particular, we demonstrated that 5 strongly binds (18.0 nM ± 2.5 nM) MMP-9, the most relevant MMP responsible of ocular surface damages in induced dry eyes syndrome (DES).

Bioorganic & Medicinal Chemistry published new progress about Dry eye syndrome. 87905-98-4 belongs to class alcohols-buliding-blocks, name is Benzyl (5-hydroxypentyl)carbamate, and the molecular formula is C13H19NO3, Quality Control of 87905-98-4.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Fuse, Shinichiro published the artcileDesign and synthesis of 2-phenyl-1,4-dioxa-spiro[4.5]deca-6,9-dien-8-ones as potential anticancer agents starting from cytotoxic spiromamakone A, Application In Synthesis of 92093-23-7, the main research area is aryldioxaspirodecadienone spiromamakone A analog preparation antitumor activity; Anticancer agent; IXNMJGORXMJZOQ-KGLIPLIRSA-N; Spiroacetal; Spirocycle; Spiromamakone A; Spiropreussione B.

The spirocycle is a key structure found in many bioactive compounds From the cytotoxic and spirocyclic natural product, spiromamakone A (I) and its analogs, a more synthetically accessible spiroacetal template was designed based on structural similarity anal. A total of 50 compounds were rapidly synthesized in only one or two synthetic steps from the starting compound, and their cytotoxicity was evaluated. As a result, (±)-(2R*,5R*)-2-(4-iodophenyl)-7-chloro-1,4-dioxa-spiro[4.5]deca-6,9-dien-8-one (II) was discovered and found to be fifteen-fold more cytotoxic than I. The easily accessible spiroacetal II appeared to act in a manner similar to the highly oxidized natural product, spiromamakone A (I).

European Journal of Medicinal Chemistry published new progress about Antitumor agents. 92093-23-7 belongs to class alcohols-buliding-blocks, name is 1-(4-Bromophenyl)ethane-1,2-diol, and the molecular formula is C8H9BrO2, Application In Synthesis of 92093-23-7.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts