(+)-N-benzyloxycarbonyl-γ,δ-dehydro-allo-coronamic acid methyl ester | 160002-57-3

• 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: (+)-N-benzyloxycarbonyl-γ,δ-dehydro-allo-coronamic acid methyl ester
• 英文别名: methyl (1S,2S)-(+)-1-N-benzyloxycarbonylamino-2-vinylcyclopropanecarboxylate；methyl (1S,2S)-2-ethenyl-1-(phenylmethoxycarbonylamino)cyclopropane-1-carboxylate
• CAS: 160002-57-3
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: YXVPMMVHJXXGIC-DOMZBBRYSA-N

物化性质

• 沸点：
  396.6±42.0 °C(predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-N-benzyloxycarbonyl-γ,δ-dehydro-allo-coronamic acid methyl ester 在 palladium dihydroxide 盐酸 、 甲醇 、 sodium hydroxide 、 氢气 、 methyloxirane 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (1S,2R)-1-氨基-2-乙基环丙烷羧酸
  参考文献：
  名称：

  Enantioselective total syntheses of (−)-allo-coronamic acid, (−)-(Z)-2,3-methanohomoserine, and (2S,3R)-Cbz-cyclo-Asp-OMe

  摘要：

  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.

  DOI：

  10.1016/0957-4166(95)00234-g
• 作为产物：
  描述：

  (±)-Z-α-膦酰甘氨酸三甲酯 在 1,3-二甲基-2-苯基-2-磷杂咪唑烷 、 盐酸 、 甲醇 、 二苯甲酮 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 32.8h， 生成 (+)-N-benzyloxycarbonyl-γ,δ-dehydro-allo-coronamic acid methyl ester
  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

• Highly efficient and stereocontrolled synthetic route to enantiopure ACC derivatives
  作者：José M. Jiménez、Ramon Casas、Rosa M. Ortuño

  DOI：10.1016/s0040-4039(00)78226-8

  日期：1994.8

  Highly diastereoselective cyclopropanation of a chiral α,β-dehydroamino acid derivative, obtained from D-mannitol, leads to a single isomer which has been transformed into the title compound in 65% overall yield. This product can be a useful intermediate in the synthesis of enantiopure ACC derivatives.

  由D-甘露糖醇获得的手性α，β-脱氢氨基酸衍生物的高度非对映选择性环丙烷化产生单一异构体，该异构体以65％的总收率转化为标题化合物。该产物可能是合成对映纯ACC衍生物的有用中间体。
• 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.
• Enantioselective total syntheses of cyclopropane amino acids: Natural products and protein methanologs
  作者：JoséM. Jiménez、Joan Rifé、Rosa M. Ortuño

  DOI：10.1016/0957-4166(96)00038-9

  日期：1996.2

  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.