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Dérivés C‐glycosyliques XXVI . Nouvelles voies d'accès à des C ‐nucléosides isoxazoliques et thiophéniques Communication préliminaire
Author(s) -
Tronchet Jean M. J.,
Martin Olivier,
Zumwald JeanBernard,
LeHong Nghiep,
Perret Françoise
Publication year - 1975
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19750580627
Subject(s) - chemistry , electrophile , stereochemistry , carbohydrate chemistry , carbohydrate , carbon fibers , medicinal chemistry , organic chemistry , catalysis , materials science , composite number , composite material
3‐ O ‐benzyl (and 3‐ O ‐methyl)‐1,2‐ O ‐isopropylidene‐α‐D‐ xylo ‐dialdo‐1,4‐furanoses treated with bromocyanomethylidene‐ or bromoacylmethylidene‐triphenylphosphoranes gave in good yields the corresponding olefinic sugars. These compounds, which bear three adjacent electrophilic carbon atoms (C(5), C(6), C(7)) constitute useful synthetic intermediates in carbohydrate chemistry. They represent, for example, good starting materials for the preparation of 3‐glycosylisoxazoles, 5‐glycosylisoxazoles and 2‐glycosylthiophenes.