VERSATILE STEREOSELECTIVE SYNTHESIS OF COMPLETELY PROTECTED TRIFUNCTIONAL ALPHA-METHYLATED ALPHA-AMINO-ACIDS STARTING FROM ALANINE

被引：54

作者：

ALTMANN, E ^{[1
]}

NEBEL, K ^{[1
]}

MUTTER, M ^{[1
]}

机构：

[1] UNIV LAUSANNE, CHIM SECT, 2 RUE BARRE, CH-1005 LAUSANNE, SWITZERLAND

来源：

HELVETICA CHIMICA ACTA | 1991年 / 74卷 / 04期

关键词：

D O I：

10.1002/hlca.19910740414

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new route to completely protected alpha-methylated alpha-amino acids starting from alanine is described (see Scheme). These derivatives, which are obtained via base-catalyzed opening of the oxazolidinones (2S,4R)- and (2R,4S)-2, can be directly employed in peptide synthesis. The synthesis of both enantiomers of Z-protected alpha-methylaspartic acid beta-(tert-butyl)ester (O4-(tert-butyl) hydrogen 2-methylaspartates (R) or (S)4a, alpha-methylglutamic acid gamma-(tert-butyl) ester (O5-(tert-butyl) hydrogen 2-methylglutamate (R)- or (S)-4b), and of N-epsilon-bis-Boc-protected alpha-methyllysine (N6 ,N6-bis[(tert-butyloxy)carbonyl]-2-methyllysine (R)-or (S)-4c) is described in full detail.

引用

页码：800 / 806

页数：7

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