Bone collagen cross-links: an efficient one-pot synthesis of (+)-pyridinoline and (+)-deoxypyridinoline

Authors
Adamczyk, M Johnson, DD Reddy, RE
Citation
M. Adamczyk et al., Bone collagen cross-links: an efficient one-pot synthesis of (+)-pyridinoline and (+)-deoxypyridinoline, TETRAHEDR-A, 11(11), 2000, pp. 2289-2298
Citations number
37
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
11
Year of publication
2000
Pages
2289 - 2298
Database
ISI
SICI code
0957-4166(20000616)11:11<2289:BCCAEO>2.0.ZU;2-6
Abstract
A one-pot reaction of (2S, 5R)-(-)-tert-butyl-[(2-tert-butoxycarbonyl)amino ]-5-hydroxy-6-amino-hexanoate 2b or (S)-(-)-tert-butyl-[(2-tert-butoxycarbo nyl)amino]-6-aminohexanoate 2c with (S)-(-)-tert-butyl-6-bromo-[bis-(2-tert -butoxycarbonyl)amino]-5-oxohexanoate 5 in the presence of K2CO3 in MeCN-Me OH followed by hydrolysis gave bone collagen cross-links, (+)-Pyd 1b or (+) -Dpd 1c, in 42-48% yield, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.