83921-73-7

Basic information

• Product Name: benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1<*>4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• CAS NO: 83921-73-7
• Molecular Weight: 1495.81
• Mol File: 83921-73-7.mol

Chemical Properties

• CAS DataBase Reference: benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1<*>4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1<*>4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside(83921-73-7)
• EPA Substance Registry System: benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1<*>4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside(83921-73-7)

Safety Data

• Hazardous Substances Data: 83921-73-7(Hazardous Substances Data)

Upstream product

• 59935-49-8 benzyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 148968-90-5 2,3,6-tris-O-(phenylmethyl)-4-O-[2,3,4,6-tetrakis-O-(phenylmethyl)-β-D-glucopyranosyl]-D-glucopyranoside 

Relevant articles and documents

Dehydrative Glycosylation Using Heptabenzyl Derivatives of Glucobioses and Lactose

Dehydrative glycosylations of the 2-, 3-, 4-, and 6-OH groups of D-glucopyranose with hepta-O-benzyl derivatives of glucobioses (O-D-glucopyranosyl-(1->n)-D-glucopyranose; n = 2, 3, 4, or 6) and lactose, in the presence of a ternary mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine in dichloromethane showed that the selectivity of the reaction depended on the anomeric configuration and the linking position to the reducing tribenzylglucose moiety of the nonreducing tetrabenzylglucosyl residue and on the class of the OH group to be glycosylated.The use of a quaternary mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, N,N-dimethylacetamide, and triethylamine made all but the β(1->2)-linked biosyl donor undergo α-condensation.Several new linear trisaccharides were obtained via debenzylation of the condensates.

STEREOSELECTIVITY IN THE DEHYDRATIVE GLYCOSYLATION WITH HEPTA-O-BENZYL-GLUCOBIOSES

Dehydrative glycosylation of benzyl 2,3,4-tri-O-benzyl α-D-glucopyranoside with hepta-O-benzyl-kojibiose, -sophorose, -nigerose, -laminaribiose, -maltose, -cellobiose, -isomaltose, and -gentiobiose gave 16 linear trisaccharide derivatives.The reaction of α(1->2)-, β(1->3)-, α(1->4)-, and β(1->6)-linked biose derivatives shows the α-selectivity, while the reaction of the others does the β-selectivity.