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Application of the Wharton Rearrangement for the de novo Synthesis of Pyranosides with ido , manno , and colito Stereochemistry
Author(s) -
Cuccarese Michael F.,
Wang HuaYu Leo,
O'Doherty George A.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300051
Subject(s) - chemistry , stereochemistry , epoxide , glycosylation , catalysis , organic chemistry , biochemistry
A de novo asymmetric synthesis of α‐ ido ‐pyranosides, as well as several deoxy and amino variants, has been achieved. The procedure involves a palladium(0)‐catalyzed glycosylation in combination with a Wharton rearrangement/epoxide‐opening reaction sequence to access sugars with ido , manno , and colito stereochemistry as well as several azido analogues.
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