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

被引:37
作者
Adamczyk, M [1 ]
Johnson, DD [1 ]
Reddy, RE [1 ]
机构
[1] Abbott Labs, Div Diagnost, Div Organ Chem Res, Abbott Pk, IL 60064 USA
关键词
D O I
10.1016/S0957-4166(99)00055-5
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
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) was described from (4S)-5-(tert-butoxy)-4-[(tert-butoxycarbonyl)amino]-5-oxopentanoic acid (6) in six steps. Also, an improved synthesis of iodide (2S)-(-)-4b was presented. (C) 1999 Elsevier Science Ltd. All rights reserved.
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收藏
页码:775 / 781
页数:7
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