Synthesis of 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans relationships

TitleSynthesis of 4-aminomethyl-tetrahydrofuran-2-carboxylates with 2,4-cis and 2,4-trans relationships
Publication TypeJournal Article
Year of Publication2006
AuthorsEdwards, AA, Sanjayan, GJ, Hachisu, S, Soengas, R, Stewart, A, Tranter, GE, Fleet, GWJ
JournalTetrahedron
Volume62
Issue17
Pagination4110-4119
Date PublishedAPR
Type of ArticleArticle
ISSN0040-4020
Keywordsgamma amino acids, Peptidomimetics, scaffolds, sugar amino acids
Abstract

Templated tetrahydrofuran-based gamma-azido esters were prepared with the C-2 and C-4 functionalities in cis and trans relative configurations. This was achieved by ring contraction of the suitably protected 2-O-triflates of pentono-1,5-lactones (D-ribose and L-arabinose) with subsequent introduction of the azide via the 4-O-triflate. Access to a corresponding beta-azido ester was achieved in good yield. Little elimination product was observed by introduction of the azide via the 3-O-triflate. These azido esters are scaffolds. which may be predisposed to adopt secondary structural motifs, for example. for use as peptidomimetics; they may also be utilised for the preparation of stereodiverse compound libraries. (c) 2006 Elsevier Ltd All rights reserved.

DOI10.1016/j.tet.2006.02.007
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.645

Divison category: 
Organic Chemistry