(1S,2R,3S,4R,1'R)-(+)-2,3-isopropylidenedioxy-4-(1'-aminomethyl-1'-hydroxy-1'-methoxycarbonylmethyl)cyclopentane-1-carboxylic acid methyl ester | 155625-66-4

• 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: (1S,2R,3S,4R,1'R)-(+)-2,3-isopropylidenedioxy-4-(1'-aminomethyl-1'-hydroxy-1'-methoxycarbonylmethyl)cyclopentane-1-carboxylic acid methyl ester
• CAS: 155625-66-4
• 化学式: C₁₄H₂₃NO₇
• 分子量: 317.339
• InChiKey: PKCQEBGLNLBLRL-MNBYSHRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.82
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  117.31
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,4R,1'R)-(+)-2,3-isopropylidenedioxy-4-(1'-aminomethyl-1'-hydroxy-1'-methoxycarbonylmethyl)cyclopentane-1-carboxylic acid methyl ester 、 (2R,3S)-Cbz-cyclo-Asp-OMe 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 以72%的产率得到methyl (1R,2S,2'R)-(-)-1-[N-(benzyloxycarbonyl)amino]-2-[2'-hydroxy-2'-methoxycarbonyl-2'-([1R,2S,3R,4S]-2,3-isopropylidenedioxy-4-methoxycarbonylcyclopent-1-yl)ethylaminocarbonyl]cyclopropane-1-carboxylate
  参考文献：
  名称：

  Enantioselective synthesis of novel, highly conformationally constrained peptide surrogates

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(97)00265-6
• 作为产物：
  描述：

  (1S,2R,3S,4R,1'R)-(+)-2,3-isopropylidenedioxy-4-(1'-azidomethyl-1'-hydroxy-1'-methoxycarbonylmethyl)cyclopentane-1-carboxylic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以100%的产率得到(1S,2R,3S,4R,1'R)-(+)-2,3-isopropylidenedioxy-4-(1'-aminomethyl-1'-hydroxy-1'-methoxycarbonylmethyl)cyclopentane-1-carboxylic acid methyl ester
  参考文献：
  名称：

  立体选择性合成新的同手性多官能侧链环戊烷衍生物

  摘要：

  立体选择性地合成了一种新的均手性多官能环戊烷衍生物，该衍生物在侧链上含有一个环氧乙烷环。该化合物是合成诸如羟基酯，多元醇或氨基醇的产物时有用的中间体。

  DOI：

  10.1016/s0957-4166(00)80480-2

文献信息

• Enantioselective synthesis of chiral polyfunctional cyclopentane derivatives: Epoxy esters, hydroxy esters, and hydroxy amino esters
  作者：Miguel Díaz、Vicenç Branchadell、Antoni Oliva、Rosa M. Ortuño

  DOI：10.1016/0040-4020(95)00745-t

  日期：1995.10

  blocks which have been used as versatile precursors to several enantiopure title compounds, these being molecules with a high functional density that bear, at least, four stereogenic centers in the cyclopentane ring and a quaternary stereocenter in the side-chain.

  通过重氮甲烷与对映体环戊基酮的羰基各自的环加成反应，以有效和非对映选择性的方式合成了对映体环氧化物。这些环氧衍生物是有效的合成构件，已用作几种对映纯标题化合物的多用途前体，这些化合物是具有高功能密度的分子，至少在环戊烷环中带有四个立体异构中心，在侧面具有四级立体中心。链。
• 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.
• Stereoselective synthesis of new homochiral polyfunctional side-chain cyclopentane derivatives
  作者：Miguel Díaz、Javier Ibarzo、Rosa M. Ortuño

  DOI：10.1016/s0957-4166(00)80480-2

  日期：1994.1

  A new homochiral polyfunctional cyclopentane derivative, containing an oxirane ring in a side-chain, has been synthesized stereoselectively . This compound is an useful intermediate in the synthesis of products such as hydroxyesters, polyols or aminoalcohols.

  立体选择性地合成了一种新的均手性多官能环戊烷衍生物，该衍生物在侧链上含有一个环氧乙烷环。该化合物是合成诸如羟基酯，多元醇或氨基醇的产物时有用的中间体。