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Incidence and Avoidance of Stereospecific 1,2-Ethylthio Group Migration During the Synthesis of Ethyl 1-Thio-α-l-rhamnopyranoside 2,3-Orthoester by France-Isabelle Auzanneau; David R. Bundle is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

What is Incidence and Avoidance of Stereospecific 1,2-Ethylthio Group Migration During the Synthesis of Ethyl 1-Thio-α-l-rhamnopyranoside 2,3-Orthoester about?

The 1,Zmigration of an ethylthio group with inversion of configuration at the C-l and C-2 atoms was observed during the attempted preparation of 2,3-orthocster derivatives of ethyl l-thio-a-L-rhamnopyranoside. The rearrangement leading to the formation of methyl 2-thio-@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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Author

France-Isabelle Auzanneau; David R. Bundle

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0008-6215)

Published

1991

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)