Hydroxylamine derivatives as nucleophiles in Ferrier glycosylation: synthesis of aminoxy pseudoglycals

Raji Reddy, Ch. ; Srinivasa Rao, Y. ; Pavan Kumar, T. ; Venkatram Reddy, K. ; Chandrasekhar, S. (2008) Hydroxylamine derivatives as nucleophiles in Ferrier glycosylation: synthesis of aminoxy pseudoglycals Synthesis, 2008 (1). pp. 122-126. ISSN 0039-7881

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

Related URL: http://dx.doi.org/10.1055/s-2007-1000828

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.

Item Type:Article
Source:Copyright of this article belongs to Thieme Medical Publishers.
Keywords:Hydroxylamines; Ferrier Glycosylation; Pseudoglycals
ID Code:62365
Deposited On:22 Sep 2011 03:33
Last Modified:22 Sep 2011 03:33

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