Tetrahydrofuran alpha-azido esters: Precursors of anomeric alpha-amino acid monomers via radical bromination

Authors
Smith, MD Long, DD Martin, A Campbell, N Bleriot, Y Fleet, GWJ
Citation
Md. Smith et al., Tetrahydrofuran alpha-azido esters: Precursors of anomeric alpha-amino acid monomers via radical bromination, SYNLETT, (7), 1999, pp. 1151-1153
Citations number
32
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
7
Year of publication
1999
Pages
1151 - 1153
Database
ISI
SICI code
0936-5214(199907):7<1151:TAEPOA>2.0.ZU;2-D
Abstract
A general route for the synthesis of tetrahydrofuran alpha-azido esters as the equivalent of monomeric furanose anomeric alpha-amino acids is describe d. Highly selective radical bromination of a range of suitably protected ca rbohydrate C-glycosyl derivatives affords bromo-esters which undergo effici ent displacement by azide to give anomeric alpha-amino acid derivatives.