Synthesis of Methyl O-α-D-Mannosyl-(1→4)-[(3-O-methyl-α-D- mannosyl)-(1→4)-]n3-O-methyl-α-D-mannosides (n = 0, 1, and 2) via Dehydrative Glycosylation

Methyl O-α-D-mannopyranosyl-(1→4)-[(3-O-methyl-α-D-mannopyranosyl-(1→4)-]n3-O-methyl-α-D-mannopyranosides (n = 0, 1, and 2), the lowest homologs related to the 3-O-methylmannose polysaccharides (MMP) from Mycobacterium smegmatis, were synthesized via dehydrative glycosylation reactions. The reagent...

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Bibliographic Details
Published in:Bulletin of the Chemical Society of Japan 2002, Vol.75 (6), p.1301-1309
Main Authors: Hirooka, Motoko, Terayama, Megumi, Mitani, Emi, Koto, Shinkiti, Miura, Asako, Chiba, Kayo, Takabatake, Ayano, Tashiro, Takako
Format: Article
Language:English
Online Access:Get full text
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Summary:Methyl O-α-D-mannopyranosyl-(1→4)-[(3-O-methyl-α-D-mannopyranosyl-(1→4)-]n3-O-methyl-α-D-mannopyranosides (n = 0, 1, and 2), the lowest homologs related to the 3-O-methylmannose polysaccharides (MMP) from Mycobacterium smegmatis, were synthesized via dehydrative glycosylation reactions. The reagent systems, composed of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine, of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and 1, 8-diazabicyclo[5.4.0]undec-7-ene, and of trimethylsilyl trifuloromethanesulfonate and pyridine were useful.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.75.1301