Regioselective halogenation of pentono-1,4-lactones. Efficient synthesis of 5-chloro- and 5-bromo-5-deoxy derivatives

Treatment of unprotected d-ribono, d-arabinono and d-xylono-1,4-lactones with either thionyl chloride or thionyl bromide in dimethylformamide led to 5-chloro- or 5-bromo-5-deoxy derivatives in 70%–95% yields. Under the same conditions, d-lyxono-1,4-lactone resulted in the 2-halogeno compounds. Graph...

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Bibliographic Details
Published in:Carbohydrate research 1997-05, Vol.300 (2), p.139-142
Main Authors: Bouchez, Véronique, Stasik, Imane, Beaupère, Daniel, Uzan, Raoul
Format: Article
Language:English
Subjects:
5-bromo-5-deoxy-pentono-1,4-lactone
5-chloro-5-deoxy-pentono-1,4-lactone
Dimethylformamide
Pentono-1,4-lactones
Regioselective halogenation
Thionyl bromide
Thionyl chloride
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Summary:Treatment of unprotected d-ribono, d-arabinono and d-xylono-1,4-lactones with either thionyl chloride or thionyl bromide in dimethylformamide led to 5-chloro- or 5-bromo-5-deoxy derivatives in 70%–95% yields. Under the same conditions, d-lyxono-1,4-lactone resulted in the 2-halogeno compounds. Graphic
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(97)00044-X