Selective cleavage of 2,3-O-isopropylidene group: a case of anchimeric assistance from O-glycoside

Wakharkar, Radhika D. ; Sahasrabuddhe, Manjusha B. ; Borate, Hanumant B. ; Gurjar, Mukund K. (2004) Selective cleavage of 2,3-O-isopropylidene group: a case of anchimeric assistance from O-glycoside Synthesis, 11 . pp. 1830-1834. ISSN 0039-7881

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Official URL: http://www.thieme-connect.com/ejournals/abstract/s...

Related URL: http://dx.doi.org/10.1055/s-2004-829128

Abstract

Alkyl 2,3-O-isopropylidene-5-O-methoxymethylfuranoside derivatives undergo selective cleavage of the 2,3-O-isopro-pylidene group, if oriented cis to the O-glycoside, in the presence of trifluoroacetic acid. Otherwise, the cleavage of the 5-O-methoxy-methyl group is favoured over the 2,3-O-isopropylidene group.

Item Type:Article
Source:Copyright of this article belongs to Thieme Medical Publishers Inc.
Keywords:Carbohydrate; Protecting Groups; Acetals; Cleavage; Isopropylidene
ID Code:11406
Deposited On:09 Nov 2010 06:09
Last Modified:02 Jun 2011 09:49

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