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Anomerization and transglycosylation reactions of permethylated methyl d-glycopyranosides

✍ Scribed by Chang Kiu Lee; Eun Ju Kim; In-Sook Han Lee

Publisher: Elsevier Science
Year: 1993
Tongue: English
Weight: 677 KB
Volume: 240
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(93)84183-7

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✦ Synopsis

The anomerization reactions of permethylated methyl o-glycopyranosides in the presence of various Lewis acid catalysts, such as Me,SiOTf, Me,SiOMs, BF,.OEt,, or TiCI, were examined in dichloromethane solution. p Anomers of the glycosides anomerized to the (Y anomer very rapidly, but the anomerizations in the opposite direction were slower. Transglycosylation reactions of the glycosides in the presence of similar catalysts and ethanol gave preferably the (Y anomers with most substrates employed. No anomerization was observed in the case of the a-mannoside, probably because the (Y anomer is strongly favored at equilibrium. Nevertheless, transglycosylation took place.

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