methyl ester of (Z)-(R)-N-Boc-6-amino-7-hydroxy-4-heptenoic acid | 133626-09-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl ester of (Z)-(R)-N-Boc-6-amino-7-hydroxy-4-heptenoic acid
• 英文别名: methyl (Z,6R)-7-hydroxy-6-[(2-methylpropan-2-yl)oxycarbonylamino]hept-4-enoate
• CAS: 133626-09-2
• 化学式: C₁₃H₂₃NO₅
• 分子量: 273.329
• InChiKey: BJBFEHMQTNCKIP-ONRRBMGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl ester of (Z)-(R)-N-Boc-6-amino-7-hydroxy-4-heptenoic acid 在 重铬酸吡啶 、 4 A molecular sieve 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (Z)-(R)-2-tert-Butoxycarbonylamino-hept-3-enedioic acid 7-methyl ester 、 (Z)-(S)-2-tert-Butoxycarbonylamino-hept-3-enedioic acid 7-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：

  (Z)-(R)-N-Boc-2,2-dimethyl-4-(4-carboxy-1-butenyl)oxazolidine 在 Dowex 50W strong H⁺ resin 、 水 作用下， 以 乙醚 、 乙腈 为溶剂， 生成 methyl ester of (Z)-(R)-N-Boc-6-amino-7-hydroxy-4-heptenoic acid
  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

文献信息

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

  DOI：——

  日期：——