Abstract

The 1,2-migration of an ethylthio group with inversion of configuration at the C-1 and C-2 atoms was observed during the attempted preparation of 2,3-orthoester derivatives of ethyl 1-thio-α- l-rhamnopyranoside. The rearrangement leading to the formation of methyl 2-thio-β- l-glucopyranosides could be avoided by preparing the orthoester in DMF rather than in acetonitrile and by using a controlled amount of acid catalyst.

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