methyl (1S,2R,4'S)-(-)-1-N-tert-butoxycarbonylamino-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropanecarboxylate | 171514-00-4

• 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,4'S)-(-)-1-N-tert-butoxycarbonylamino-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-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopropane-1-carboxylate
• CAS: 171514-00-4
• 化学式: C₁₅H₂₅NO₆
• 分子量: 315.367
• InChiKey: JQBMWKSFIXEVOB-WMFXKJRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 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-tert-butoxycarbonylamino-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)cyclopropanecarboxylate 在 盐酸 、 甲醇 、 sodium periodate 作用下， 以 四氢呋喃 为溶剂， 反应 2.83h， 生成 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 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-tert-butoxycarbonylamino-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

• Enantioselective synthesis of cyclopropane aminoalcohols containing quaternary stereogenic centers
  作者：Joan Rifé、Rosa M. Ortuño

  DOI：10.1016/s0957-4166(99)00463-2

  日期：1999.10

  Some title compounds have been synthesized in enantiomerically pure form starting from d- or l-glyceraldehyde as chiral precursors. A new synthesis of (+)-(Z)-methanohomoserine, one of the key intermediates employed, is also described. The target molecules are densely functionalized. Thus, in addition to one or two hydroxyl groups on a side-chain, an amino group is attached to a quaternary carbon of

  从对-或1-甘油醛作为手性前体开始，已经以对映体纯的形式合成了一些标题化合物。还描述了一种新合成的（+）-（Z）-甲氨基高丝氨酸，它是所使用的关键中间体之一。靶分子被密集地官能化。因此，除了侧链上的一个或两个羟基之外，氨基还连接到环丙烷环的季碳上，并且该立体中心的第四取代基包含卤素原子，烷基或环氧基。具有醇，硫醚或酯的功能。这些化合物中的一些在合成新的环丙烷核苷中是有用的前体。
• 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.