(Z)-(S)-2-<<(benzyloxy)carbonyl>amino>-8-<<(tert-butyloxy)carbonyl>amino>-3-octenoic acid, methyl ester | 133626-18-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-(S)-2-<<(benzyloxy)carbonyl>amino>-8-<<(tert-butyloxy)carbonyl>amino>-3-octenoic acid, methyl ester
• CAS: 133626-18-3
• 化学式: C₂₂H₃₂N₂O₆
• 分子量: 420.506
• InChiKey: PPAXDXOFXRHRAZ-BLSFAOBESA-N

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 (Z)-(R)-2-<<(benzyloxy)carbonyl>amino>-8-<<(tert-butyloxy)carbonyl>amino>-3-octenoic acid 以 乙醚 为溶剂， 生成 (Z)-(S)-2-<<(benzyloxy)carbonyl>amino>-8-<<(tert-butyloxy)carbonyl>amino>-3-octenoic acid, methyl ester 、 (Z)-(R)-2-<<(benzyloxy)carbonyl>amino>-8-<<(tert-butyloxy)carbonyl>amino>-3-octenoic acid, methyl ester
  参考文献：
  名称：

  Synthesis of chiral vinylglycines

  摘要：

  (R)- or (S)-benzyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7a) and (R)- or (S)-1,1-dimethylethyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7b), readily available from serine, react with Wittig reagents to give alkenes 8. Selective deprotection followed by oxidation of the resulting unsaturated amino alcohols 9 provides vinylglycines 5 of defined configuration (> 95% ee) and double-bond geometry. D-Vinylglycines are obtained from L-serine, and conversely, D-serine gives beta,gamma-unsaturated amino acids with the L configuration. The double-bond geometry is controlled by the nature of the phosphorous ylide employed. The scope and limitations of this new methodology for the preparation of chiral vinylglycines is examined.

  DOI：

  10.1021/jo00013a023