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Synthesis 2004(11): 1830-1834  
DOI: 10.1055/s-2004-829128
PAPER
© Georg Thieme Verlag Stuttgart · New York

Selective Cleavage of 2,3-O-Isopropylidene Group: A Case of Anchimeric Assistance from O-Glycoside

Radhika D. Wakharkar*, Manjusha B. Sahasrabuddhe, Hanumant B. Borate, Mukund K. Gurjar
National Chemical Laboratory, Pune 411008, India
Fax: +91(20)25893614; e-Mail: rdw@dalton.ncl.res.in;
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Publication History

Received 23 February 2004
Publication Date:
01 July 2004 (online)

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Abstract

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

Key words

carbohydrate - protecting groups - acetals - cleavage - isopropylidene

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