Synlett 2007(8): 1247-1250  
DOI: 10.1055/s-2007-977451
LETTER
© Georg Thieme Verlag Stuttgart · New York

A Facile and General Synthesis of Rare l-Sugar Lactones

Rawle I. Hollingsworth*a,b, Xuezheng Songb
a Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA
Fax: +1(517)3539334; e-Mail: rih@afidtherapeutics.com; e-Mail: rih@cem.msu.edu;
b Department of Biochemistry and Molecular Biology, Michigan State University, East Lansing, MI 48824, USA
Further Information

Publication History

Received 16 September 2006
Publication Date:
08 May 2007 (online)

Abstract

A facile and general synthesis of rare l-sugar lactones from d-sugars by selectively inverting C-5 was developed. Selective 1-deacylation of sugar perpivaloates by hydroxylamine is described. More practically, β-d-glucose pentaacetate could be transformed to l-idono-1,4-lactones by this simple procedure.