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Synthesis of gem ‐Difluorocarba‐ D ‐glucose: A Step Further in Sugar Mimesis
Author(s) -
Deleuze Aurélie,
Menozzi Candice,
Sollogoub Matthieu,
Sinaÿ Pierre
Publication year - 2004
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200461244
Subject(s) - steric effects , sugar , anomer , chemistry , oxygen atom , stereochemistry , biochemistry , organic chemistry , molecule
A rearrangement strategy was used for the synthesis of α‐ and β‐ gem ‐difluorocarba‐ D ‐glucose, which are close congeners of α‐ and β‐ D ‐glucose, in which the endocyclic oxygen atom has been replaced by a gem ‐difluoromethylene group (see scheme). The two anomers α or β were obtained stereoselectively by the use of steric or electronic control, respectively. TIBAL=triisobutylaluminum.
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