83158-27-4

Basic information

• Product Name: methyl 2,3-di-O-benzoyl-β-D-xylopyranoside
• Synonyms: methyl 2,3-di-O-benzoyl-β-D-xylopyranoside
• CAS NO: 83158-27-4
• Molecular Weight: 372.375
• Mol File: 83158-27-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: methyl 2,3-di-O-benzoyl-β-D-xylopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3-di-O-benzoyl-β-D-xylopyranoside(83158-27-4)
• EPA Substance Registry System: methyl 2,3-di-O-benzoyl-β-D-xylopyranoside(83158-27-4)

Safety Data

• Hazardous Substances Data: 83158-27-4(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 69984-20-9 methyl α-D-xylopyranoside 4-benzyl ether 
• 147242-30-6 Chloro-acetic acid (3R,4R,5R,6R)-4,5-dihydroxy-6-methoxy-tetrahydro-pyran-3-yl ester 
• 488092-56-4 methyl 2,3-di-O-benzoyl-4-O-chloroacetyl-β-D-xylopyranoside 
• 612-05-5 methyl-β-D-xylopyranoside 
• 86386-90-5 methyl 2,3-di-O-benzoyl-4-O-benzyl-β-D-xylopyranoside 

Downstream Products

• 488092-65-5 methyl (methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside 
• 488092-58-6 methyl 3-O-allyl-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1->4)-2,3-di-O-benzoyl-β-D-xylopyranoside 
• 87461-39-0 C₂₃H₂₈O₇Si 

Relevant articles and documents

A practical synthesis of β-D-GlcA-(1→3)-β-D-Gal-(1→3)-β-D-Gal-(1→4)-D- Xyl, a part of the common linkage region of a glycosaminoglycan

A practical synthesis of β-D-GlcA-(1→3)-β-D-Gal-(1→3)-β-D-Gal-(1→4)- β-D-Xyl-(1→OMe) was achieved by coupling of methyl 2,3,4-tri-O-acetyl-α-D-glucopyranosyluronate trichloroacetimidate with a trisaccharide acceptor. The trisaccharide acceptor was obtained by condensation of 3-O-allyl-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl-(1→3)-2,4,6- tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate with methyl 2,3-di-O-benzoyl-β-D-xylopyranoside, followed by deallylation. The β-(1→3)-linked disaccharide was prepared readily with p-methoxyphenyl 3-O-allyl-2,4,6-tri-O-benzoyl-β-D-galactopyranoside as the key synthon. The α-(1→3)-linkage was formed in considerable amount with galactose mono- and disaccharide trichloroacetimidate donors with C-2 neighboring group participation.

Regioselective Monoacylation of Some Glycopyranosides via Cyclic Tin Intermediates

Selective mono-benzoylation of some pento- and hexo-pyranosides (Me β-L-Ara, Ph α-L-Ara, Me α-D-Xyl, Me β-D-Xyl, Me α-D-Glc, Me-β-D-Glc, Me α-D-Gal, Me β-D-Gal, and Me α-D-Man) by using Bu2SnO was examined in comparaison with the results of the (Bu3Sn)2O method and direct benzoylation.The Bu2SnO method is particularly useful in that it selectively activates an equatorial hydroxyl group wich bears an oxygenated function (OH or OMe) in a cis relationship at an adjacent position, even in the presence of a more reactive primary OH group.The various mono- and di-O-benzoyl derivatives prepared in this work were unambiguously identified by analysis of their 13C-nuclear magnetic resonance spectra.