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Synthesis 2004(11): 1830-1834
DOI: 10.1055/s-2004-829128
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
Weitere Informationen
Received
23 February 2004
Publikationsdatum:
01. Juli 2004 (online)
Publikationsverlauf
Publikationsdatum:
01. Juli 2004 (online)

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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