(R)-2-Cyano-3-hydroxy-2-methyl-propionic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester | 219567-02-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (R)-2-Cyano-3-hydroxy-2-methyl-propionic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
• 英文别名: [(1S,2R,4R)-1-(dicyclohexylsulfamoylmethyl)-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] (2R)-2-cyano-3-hydroxy-2-methylpropanoate
• CAS: 219567-02-9
• 化学式: C₂₇H₄₄N₂O₅S
• 分子量: 508.723
• InChiKey: FISQYANNIPAMPW-CYPYXQILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  107.7
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-2-Cyano-3-hydroxy-2-methyl-propionic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester 在 lithium hydroxide 、 phosphorus pentoxide 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.25h， 生成 (2R)-2-cyano-3-(methoxymethoxy)-2-methylpropanoic acid
  参考文献：
  名称：

  Synthesis of (S)-N-tert-butoxycarbonyl-N,O-isopropylidene-α-methylserinal: A potential building block for the asymmetric synthesis of non-natural amino acids

  摘要：

  The title compound (S)-alpha-methylserinal acetonide has been efficiently prepared from (S)-alpha-methylserine, which is readily available in enantiomerically pure form by Curtius rearrangement of alpha,alpha-dialkyl 2-cyanoesters obtained by diastereoselective alkylation of (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyanopropanoate using methoxymethyl iodide or paraformaldehyde as electrophiles by an extension of our recently developed methodology for the synthesis of alpha,alpha-dialkylamino acids, (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00937-5
• 作为产物：
  描述：

  聚合甲醛 、 (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyanopropanoate 在 lithium diisopropyl amide 作用下， 生成 、 (R)-2-Cyano-3-hydroxy-2-methyl-propionic acid (1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
  参考文献：
  名称：

  Synthesis of (S)-N-tert-butoxycarbonyl-N,O-isopropylidene-α-methylserinal: A potential building block for the asymmetric synthesis of non-natural amino acids

  摘要：

  The title compound (S)-alpha-methylserinal acetonide has been efficiently prepared from (S)-alpha-methylserine, which is readily available in enantiomerically pure form by Curtius rearrangement of alpha,alpha-dialkyl 2-cyanoesters obtained by diastereoselective alkylation of (1S,2R,4R)-10-dicyclohexylsulfamoylisobornyl 2-cyanopropanoate using methoxymethyl iodide or paraformaldehyde as electrophiles by an extension of our recently developed methodology for the synthesis of alpha,alpha-dialkylamino acids, (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00937-5