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Reaction of carbohydrates with Vilsmeier reagent: a tandem selective chloro O-formylation of sugars.
Org Biomol Chem
; 7(7): 1280-3, 2009 Apr 07.
Article
in English
| MEDLINE
| ID: mdl-19300809
ABSTRACT
A convenient and efficient method for selective replacement of the primary hydroxyl groups of sugars by chlorine with concomitant O-formylation, compatible with the presence of a variety of functional groups, has been developed using the Vilsmeier-Haack reaction. Sugars having free primary hydroxyl groups mostly afforded the chloro-O-formylated product while sugars devoid of primary hydroxyl groups yielded only O-formylated products.