121123-33-9Relevant articles and documents
Stereoselective α-Glucosylation with Tetra-O-benzyl-α-D-glucose and a Mixture of Trimethylsilyl Bromide, Cobalt(II) Bromide, Tetrabutylammonium Bromide, and a Molecular Sieve. A Synthesis of 3,6-Di-O-(α-D-glucopyranosyl)-D-glucose
Koto, Shinkiti,Morishima, Naohiko,Kusuhara, Chiharu,Sekido, Shigeko,Yoshida, Toyosaku,Zen, Shonosuke
, p. 2995 - 2999 (2007/10/02)
A mixture of trimethylsilyl bromide, cobalt(II) bromide, tetrabutylammonium bromide, and a molecular sieve (4A) is effective for the stereoselective, one-stage α-glucosylation of alcohol with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose in dichloromethane.Using this procedure, several disaccharide derivatives as well as O-α-D-glucopyranosyl-(1 -> 3)-O- 6)>-D-glucopyranose are synthesized.
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.