(E)-(R)-N-Cbz-2,2-dimethyl-4-(2-carboxyethenyl)oxazolidine methyl ester | 133625-95-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-(R)-N-Cbz-2,2-dimethyl-4-(2-carboxyethenyl)oxazolidine methyl ester
• 英文别名: benzyl (4R)-4-[(E)-3-methoxy-3-oxoprop-1-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 133625-95-3
• 化学式: C₁₇H₂₁NO₅
• 分子量: 319.357
• InChiKey: LJGKTWKOUNRGCB-ATWMFIQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-(R)-N-Cbz-2,2-dimethyl-4-(2-carboxyethenyl)oxazolidine methyl ester 在 Dowex 50W strong H⁺ resin 、 水 作用下， 以 甲醇 为溶剂， 以89%的产率得到(E)-(R)-N-Cbz-4-amino-5-hydroxy-2-pentenoic 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
• 作为产物：
  描述：

  (4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde 以85%的产率得到
  参考文献：
  名称：

  BEAULIEU, PIERRE L.;DUCEPPE, JEAN-SIMON;JOHNSON, CAROLYNE, J. ORG. CHEM., 56,(1991) N3, C. 4196-4204

  摘要：

  DOI：

文献信息

• Excess sodium ions improve Z selectivity in Horner–Wadsworth–Emmons olefinations with the Ando phosphonate
  作者：Petri M. Pihko、Taina M. Salo

  DOI：10.1016/s0040-4039(03)00935-3

  日期：2003.6

  New, improved conditions for Z selective Horner-Wadsworth-Emmons olefinations with Ando's bis(o-methylphenyl)phosphonates are reported. A combination of NaH and Nal affords Z olefins in up to >99:1 selectivity and good yields. (C) 2003 Elsevier Science Ltd. All rights reserved.