77988-11-5Relevant articles and documents
ONE-STAGE GLYCOSYLATION USING PROTECTED GLYCOSE: THE SYNTHESIS OF O-β-D-GLUCOPYRANOSYL-(1->3)-O-6)>-D-GLUCOPYRANOSE
Koto, Shinkiti,Inada, Shigeru,Yoshida, Toyosaku,Toyama, Miyako,Zen, Shonosuke
, p. 255 - 259 (2007/10/02)
The one-stage β-glycosilation of benzyl 3-O-acetyl-2,4-di-O-benzyl-α-D-glucopyranoside ( 1 ) with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose ( 2 ) using a mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine, followed by deacetylation, gave benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->6)-2,4-di-O-benzyl-α-D-glucopyranoside ( 3 ).The disaccharide derivative 3 was then subjected to the β-glucosylation, followed by catalytic hydrogenation, to afford O-β-D-glucopyranosyl-(1->3)-O-6)>-D-glucopyranose ( 4 ).The key intermediate 1 was prepared from D-glucose by way of a Fischer reaction, triphenylmethylation, a controlled benzylation, and detriphenylmethylation.