Hydroxylamine Derivatives as Nucleophiles in Ferrier Glycosylation: Synthesis of Aminoxy Pseudoglycals [1]

Abstract

The use of hydroxylamine derivatives as the aminoxy equivalent nucleophiles in Ferrier glycosylation catalyzed by various acid catalysts is described. The reaction of tri-O-protected d-glucal with N-hydroxyphthalimide or N-hydroxysuccinimide was effectively promoted by a catalytic amount of zinc(II) chloride to produce the corresponding aminoxy pseudoglycal in good yields and preferential anomeric selectivity.

Key words

hydroxylamines - Ferrier glycosylation - pseudoglycals

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IICT Communication No. 070126.

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IICT Communication No. 070126.

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This product showed hypolipidemic activity in mice, see ref. 12.