Collagen cross-links: a convenient synthesis of tert-butyl-(2S)-2-[(tert-butoxycarbonyl)amino]-4-(2-oxiranyl)butanoate

Authors
Adamczyk, M Johnson, DD Reddy, RE
Citation
M. Adamczyk et al., Collagen cross-links: a convenient synthesis of tert-butyl-(2S)-2-[(tert-butoxycarbonyl)amino]-4-(2-oxiranyl)butanoate, TETRAHEDR-A, 10(4), 1999, pp. 775-781
Citations number
27
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
4
Year of publication
1999
Pages
775 - 781
Database
ISI
SICI code
0957-4166(19990226)10:4<775:CCACSO>2.0.ZU;2-L
Abstract
An efficient synthesis of tert-butyl-(2S)-2-[(tert-butoxycarbonyl)amino]-4- (2-oxiranyl)butanoate (5), the key intermediate for preparation of collagen cross-links (+)-pyridinoline (Pyd, 1) and (+)-deoxypyridinoline (Dpd, 2) w as described from (4S)-5-(tert-butoxy)-4-[(tert-butoxycarbonyl)amino]-5-oxo pentanoic acid (6) in six steps. Also, an improved synthesis of iodide (2S) -(-)-4b was presented. (C) 1999 Elsevier Science Ltd. All rights reserved.