methyl (1S,2R,4'S)-(-)-1-N-benzyloxycarbonylamino-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropanecarboxylate | 160002-54-0

• 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: methyl (1S,2R,4'S)-(-)-1-N-benzyloxycarbonylamino-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropanecarboxylate
• 英文别名: methyl (1S,2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-(phenylmethoxycarbonylamino)cyclopropane-1-carboxylate
• CAS: 160002-54-0
• 化学式: C₁₈H₂₃NO₆
• 分子量: 349.384
• InChiKey: AAGKHCUELJJIMG-IYOUNJFTSA-N

物化性质

• 沸点：
  467.8±45.0 °C(predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (1S,2R,4'S)-(-)-1-N-benzyloxycarbonylamino-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropanecarboxylate 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 二苯甲酮 、 potassium tert-butylate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.3h， 生成 methyl (1S,2R,4'S)-(-)-1-N-benzyloxycarbonylamino-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)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

• 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。
• Synthesis and photochemical decomposition of pyrazolines from homochiral amino pentenoates. A laser flash-photolysis study
  作者：JoséM. Jiménez、JoséL. Bourdelande、Rosa M. Ortuño

  DOI：10.1016/s0040-4020(97)00098-7

  日期：1997.3

  order to find the optimal conditions and to establish the influence of sensitizers. The transient behaviour of the pyrazoline triplet state has been analyzed by laser flash photolysis either after direct excitation or after energy transfer from benzophenone.

  光学纯的吡唑啉是通过将重氮甲烷环加成到手性氨基戊烯酸酯上而合成的，取决于前体的立体化学，面部非对映选择性是相反的。已显示这些吡唑啉光分解为相应的环丙烷是立体定向的，并且已经进行了研究，以找到最佳条件并建立敏化剂的影响。直接激发后或从二苯甲酮转移能量后，通过激光闪光光解法分析了吡唑啉三重态的瞬态行为。
• 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 synthesis of novel, highly conformationally constrained peptide surrogates
  作者：Miguel Díaz、JoséM. Jiménez、Rosa M. Ortuño

  DOI：10.1016/s0957-4166(97)00265-6

  日期：1997.7

  Two new enantiomeric peptide surrogates as well as a tripeptide, ail of them having highly conformationally constrained structures, have been synthesized. (Z)-cyclo-Aspartic acid and convenient a-substituted isoserine derivatives, in both antipodal forms, as well as methyl (R)-2-phenylglycinate, have been used as the monomeric units. (C) 1997 Elsevier Science Ltd.
• 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.