methyl (1S,2R,1'S)-(-)-1-N-tert-butoxycarbonylamino-2-(1',2'-dihydroxyethyl)cyclopropanecarboxylate | 171514-01-5

• 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: methyl (1S,2R,1'S)-(-)-1-N-tert-butoxycarbonylamino-2-(1',2'-dihydroxyethyl)cyclopropanecarboxylate
• CAS: 171514-01-5
• 化学式: C₁₂H₂₁NO₆
• 分子量: 275.302
• InChiKey: RSGXAQIGYLRALU-SXMVTHIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  105.09
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (1S,2R,1'S)-(-)-1-N-tert-butoxycarbonylamino-2-(1',2'-dihydroxyethyl)cyclopropanecarboxylate 在 sodium periodate 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以85%的产率得到methyl (1S,2R)-(-)-1-N-tert-butoxycarbonylamino-2-formylcyclopropanecarboxylate
  参考文献：
  名称：

  Enantioselective total syntheses of cyclopropane amino acids: Natural products and protein methanologs

  摘要：

  The syntheses of (-)-allo-coronamic acid, (-)-allo-norcoronamic acid, (-)-(Z)-2, 3-methanohomoserine, (-)-(Z)-2, 3-methanomethionine, and (2S, 3R)-Cbz-cyclo-Asp-OMe have been achieved in 45-68% overall yields from suitable intermediates derived from homochiral aminopentenoates which were obtained, in bun, from D-glyceraldehyde. The key synthetic step involves the quantitative and highly diastereoselective cyclopropanation of such precursors. The factors dealing with the control of stereoselectivity are highlighted and the main features in sidechain functionalization to the respective target molecules are discussed.

  DOI：

  10.1016/0957-4166(96)00038-9
• 作为产物：
  描述：

  trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate 在 盐酸 、 甲醇 、 二苯甲酮 、 potassium tert-butylate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 6.8h， 生成 methyl (1S,2R,1'S)-(-)-1-N-tert-butoxycarbonylamino-2-(1',2'-dihydroxyethyl)cyclopropanecarboxylate
  参考文献：
  名称：

  Enantioselective total syntheses of cyclopropane amino acids: Natural products and protein methanologs

  摘要：

  The syntheses of (-)-allo-coronamic acid, (-)-allo-norcoronamic acid, (-)-(Z)-2, 3-methanohomoserine, (-)-(Z)-2, 3-methanomethionine, and (2S, 3R)-Cbz-cyclo-Asp-OMe have been achieved in 45-68% overall yields from suitable intermediates derived from homochiral aminopentenoates which were obtained, in bun, from D-glyceraldehyde. The key synthetic step involves the quantitative and highly diastereoselective cyclopropanation of such precursors. The factors dealing with the control of stereoselectivity are highlighted and the main features in sidechain functionalization to the respective target molecules are discussed.

  DOI：

  10.1016/0957-4166(96)00038-9

文献信息

• Enantioselective total syntheses of (−)-allo-coronamic acid, (−)-(Z)-2,3-methanohomoserine, and (2S,3R)-Cbz-cyclo-Asp-OMe
  作者：JoséM. Jiménez、Joan Rifé、Rosa M. Ortuño

  DOI：10.1016/0957-4166(95)00234-g

  日期：1995.8

  The title amino acids have been synthesized in 45, 47, and 63% overall yields, respectively, from enantiopure aminopentenoates, easily available from D-glyceraldehyde as a source of chirality, following divergent pathways from similar diols as common key intermediate compounds.