[(1R,2S,3R,4S)-1,7,7-trimethyl-3-(naphthalen-1-ylsulfonylamino)-2-bicyclo[2.2.1]heptanyl] (2S)-2-hydroxybutanoate | 146311-12-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [(1R,2S,3R,4S)-1,7,7-trimethyl-3-(naphthalen-1-ylsulfonylamino)-2-bicyclo[2.2.1]heptanyl] (2S)-2-hydroxybutanoate
• CAS: 146311-12-8
• 化学式: C₂₄H₃₁NO₅S
• 分子量: 445.58
• InChiKey: MOUXWIQDDHAIBQ-RMSQTDAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(1R,2S,3R,4S)-1,7,7-trimethyl-3-(naphthalen-1-ylsulfonylamino)-2-bicyclo[2.2.1]heptanyl] (2S)-2-hydroxybutanoate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以89%的产率得到S-2-羟基丁酸
  参考文献：
  名称：

  .alpha.-(Arylsulfonamido)borneols as auxiliaries in asymmetric synthesis: an efficient and highly stereoselective method for the reduction of .alpha.-keto esters

  摘要：

  A method for preparation of enantiomerically pure alpha-hydroxy esters by stereoselective reduction of chiral alpha-keto esters under convenient conditions (LiAlH(OCEt3)3, THF,0-degrees-C) has been developed. The compounds exo,exo-3-(arylsulfonamido)-2-borneol and exo,exo-2-(arylsulfonamido)-3-borneol have been used as novel auxiliaries to achieve highly diastereoselective reductions. The auxiliaries can be removed by mild saponification (LiOH, THF-H2O, rt) without racemization of the reduced products.

  DOI：

  10.1021/jo00057a004
• 作为产物：
  描述：

  3-氨基-1,7,7-三甲基-双环[2,2,1]庚-2-醇 在 吡啶 、 4-二甲氨基吡啶 、 LiAlH(OCEt₃)3 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 [(1R,2S,3R,4S)-1,7,7-trimethyl-3-(naphthalen-1-ylsulfonylamino)-2-bicyclo[2.2.1]heptanyl] (2S)-2-hydroxybutanoate
  参考文献：
  名称：

  .alpha.-(Arylsulfonamido)borneols as auxiliaries in asymmetric synthesis: an efficient and highly stereoselective method for the reduction of .alpha.-keto esters

  摘要：

  A method for preparation of enantiomerically pure alpha-hydroxy esters by stereoselective reduction of chiral alpha-keto esters under convenient conditions (LiAlH(OCEt3)3, THF,0-degrees-C) has been developed. The compounds exo,exo-3-(arylsulfonamido)-2-borneol and exo,exo-2-(arylsulfonamido)-3-borneol have been used as novel auxiliaries to achieve highly diastereoselective reductions. The auxiliaries can be removed by mild saponification (LiOH, THF-H2O, rt) without racemization of the reduced products.

  DOI：

  10.1021/jo00057a004

文献信息

• .alpha.-(Arylsulfonamido)borneols as auxiliaries in asymmetric synthesis: an efficient and highly stereoselective method for the reduction of .alpha.-keto esters
  作者：Yi Bin Xiang、Ken Snow、Michel Belley

  DOI：10.1021/jo00057a004

  日期：1993.2

  A method for preparation of enantiomerically pure alpha-hydroxy esters by stereoselective reduction of chiral alpha-keto esters under convenient conditions (LiAlH(OCEt3)3, THF,0-degrees-C) has been developed. The compounds exo,exo-3-(arylsulfonamido)-2-borneol and exo,exo-2-(arylsulfonamido)-3-borneol have been used as novel auxiliaries to achieve highly diastereoselective reductions. The auxiliaries can be removed by mild saponification (LiOH, THF-H2O, rt) without racemization of the reduced products.