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

doi:10.1055/s-2004-829128

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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;

Abstract

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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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References

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