20787-15-9

Basic information

• Product Name: methyl 2,3,4-tri-O-benzyl-β-D-xylopyranoside
• Synonyms: methyl 2,3,4-tri-O-benzyl-β-D-xylopyranoside
• CAS NO: 20787-15-9
• Molecular Weight: 434.532
• Mol File: 20787-15-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: methyl 2,3,4-tri-O-benzyl-β-D-xylopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,4-tri-O-benzyl-β-D-xylopyranoside(20787-15-9)
• EPA Substance Registry System: methyl 2,3,4-tri-O-benzyl-β-D-xylopyranoside(20787-15-9)

Safety Data

• Hazardous Substances Data: 20787-15-9(Hazardous Substances Data)

Upstream product

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

Downstream Products

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

Relevant articles and documents

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.

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 assignment of the signals of benzyl methylene carbon atoms in 13C-n.m.r. spectra of per-O-benzylated methyl glycopyranosides

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