- SYNTHESIS OF A BRANCHED D-GLUCOTETRAOSE, THE REPEATING UNIT OF THE EXTRACELLULAR POLYSACCHARIDES OF Grifola umbellate, Sclerotinia libertiana, Porodisculus pendulus, AND Schizophyllum commune FRIES
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The synthesis of D-glucotetraose, 3-O--6-O-β-D-glucopyranosyl-α (and β)-D-glucopyranose, the repeating unit of the extracellular polysaccharides of Grifora umbellata, Sclerotinia libertiana, Porodisculus pendulus, and Schizophyllum commune Fries, is described.
- Ogawa, Tomoya,Kaburagi, Toshiaki
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- 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
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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.
- Koto, Shinkiti,Morishima, Naohiko,Kusuhara, Chiharu,Sekido, Shigeko,Yoshida, Toyosaku,Zen, Shonosuke
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p. 2995 - 2999
(2007/10/02)
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- ONE-STAGE GLYCOSYLATION USING PROTECTED GLYCOSE: THE SYNTHESIS OF O-β-D-GLUCOPYRANOSYL-(1->3)-O-6)>-D-GLUCOPYRANOSE
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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.
- Koto, Shinkiti,Inada, Shigeru,Yoshida, Toyosaku,Toyama, Miyako,Zen, Shonosuke
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p. 255 - 259
(2007/10/02)
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