20787-15-9

Upstream product

• 100-44-7 benzyl chloride 
• 612-05-5 methyl-β-D-xylopyranoside 
• 100-39-0 benzyl bromide 
• 87-72-9 D-Xylose 
• 91-09-8 methyl xyloside 

Downstream Products

• 20787-14-8 methyl 2,3,4-tri-O-benzyl-α-D-xylopyranoside 
• 242143-00-6 methyl 2,3,4-tri-O-benzyl-D-xylopyranoside 
• 20787-16-0 2,3,4-tri-O-benzyl-α-D-xylopyranose 

Relevant academic research and scientific papers

Analysis of UDP-D-apiose/UDP-D-xylose synthase-catalyzed conversion of UDP-D-apiose phosphonate to UDP-D-xylose phosphonate: Implications for a retroaldol-aldol mechanism

UDP-d-apiose/UDP-d-xylose synthase (AXS) catalyzes the conversion of UDP-d-glucuronic acid to UDP-d-apiose and UDP-d-xylose. An acetyl-protected phosphonate analogue of UDP-d-apiose was synthesized and used in an in situ HPLC assay to demonstrate for the first time the ability of AXS to interconvert the two reaction products. Density functional theory calculations provided insight into the energetics of this process and the apparent inability of AXS to catalyze the conversion of UDP-d-xylose to UDP-d-apiose. The data suggest that this observation is unlikely to be due to an unfavorable equilibrium but rather results from substrate inhibition by the most stable chair conformation of UDP-d-xylose. The detection of xylose cyclic phosphonate as the turnover product reveals significant new details about the AXS-catalyzed reaction and supports the proposed retroaldol-aldol mechanism of catalysis.

Process of producing 8A- and 9A-azalide antibiotics

A process of producing 8a- and 9a- azalide compounds is disclosed, comprised of reacting an 8a- aza or 9a- aza azalide eastern fragment or a derivative thereof with a compound of the formula: wherein X and Y are appropriate reactive groups and A' is a fragment or compound which forms the western portion of the azalide, and cyclizing this intermediate to form the target 8a- or 9a-azalide compound. Compounds of formula I, II and III as well as other azalides can be synthesized according to this process.

Benzylation of sugar polyols by means of the PTC method

Studies on benzylation of hydrophilic carbohydrate derivatives with benzyl chloride, using a phase-transfer technique, have led to the conclusion that alkylation of a substrate can be greatly facilitated by the introduction of a "co-catalyst" (e.g. a tertiary alcohol) and/or a co-solvent (e.g.DMSO) to the reaction mixture.Efficient procedures for benzylation of sugar derivatives having three to eight hydroxyl groups per molecule, in two-phase system employing an almost stoichiometric amount of the alkylating agent, are presented.

THE EFFECT OF REPLACING A 3-O-ACETYL GROUP BY A 3-O-BENZY; GROUP IN A METHYL 4-O-TRITYL-β-D-XYLOPYRANOSIDE DERIVATIVE ON THE EFFICIENCY OF 1,2-trans-GLYCOSYLATION WITH A D-XYLOSE 1,2-O-(1-CYANOETHYLIDENE) DERIVATIVE

Replacement of AcO-3 in methyl 2,3-di-O-acetyl-4-O-trityl-β-D-xylopyranoside with a benzyl group greatly increases the 1,2-trans-stereoselectivity of glycosylation with D-xylopyranose 1,2-O-(1-Cyanoethylidene) derivative.Anomerisation of methyl 2-O-benzyl-β-D-xylopyranoside derivatives occured under the action of triphenylmethylium perchlorate.

Pentoside Synthesis by Dehydrative Glykosylation. Synthesis of O-α-L-Arabinofuranosyl-(1-3)-O-β-D-xylopyranosyl-(1-4)-D-xylopyranose

O-α-L-Arabinofuranosyl-(1-3)-O-β-D-xylopyranosyl-(1-4)-D-xylopyranose isolated from the hydrolyzate of corncobs arabinoxylan was synthesized by way of dehydrative glycosylation.