83158-27-4

Upstream product

• 98-88-4 benzoyl chloride 
• 612-05-5 methyl-β-D-xylopyranoside 
• 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 
• 86386-90-5 methyl 2,3-di-O-benzoyl-4-O-benzyl-β-D-xylopyranoside 

Downstream Products

• 87461-39-0 C₂₃H₂₈O₇Si 
• 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 
• 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 

Relevant academic research and scientific papers

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.

13C AND 1H NMR SPECTRA OF ALL METHYL O-BENZOYL-β-D-XYLOPYRANOSIDES. NONADITIVITY OF ACYLATION EFFECTS ON 13C CHEMICAL SHIFTS IN DEUTERIOCHLOROFORM SOLUTIONS

All methyl O-benzoyl-β-D-xylopyranosides have been prepared and their 1H and 13C NMR spectra measured in deuteriochloroform solutions.The 1H NMR spectra were analysed to the first order and assigned with the aid of homonuclear decoupling.The 13C chemical

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.