(-)-3-methyl-2-<(phenylsulfonyl)methyl>butyl chloroacetate | 152615-06-0

• 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: (-)-3-methyl-2-<(phenylsulfonyl)methyl>butyl chloroacetate
• 英文别名: (-)-3-methyl-2-[(phenylsulfonyl)methyl]butyl chloroacetate；[(2S)-2-(benzenesulfonylmethyl)-3-methylbutyl] 2-chloroacetate
• CAS: 152615-06-0
• 化学式: C₁₄H₁₉ClO₄S
• 分子量: 318.821
• InChiKey: JFGHXSZQHPBDDO-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-3-methyl-2-<(phenylsulfonyl)methyl>butyl chloroacetate 在 sodium hydroxide 、 三丁基膦 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 反应 87.0h， 生成 (S)-(-)-3-methyl-2-<(phenylsulfonyl)methyl>butyl phenyl sulfide
  参考文献：
  名称：

  An enzyme-based synthesis of (S)-(−)-3-methyl-2-[(phenylsiilfonyl)-methyl]butyl phenyl sulfide and the stereochemical course of its alkylation

  摘要：

  The two title reactions have been explored. In the first instance, best results were achieved if the chloroacetate ester of 3-methyl-2[(phenylsulfonyl)methyl]-1-butanol was subjected to enzymatic hydrolysis with lipase P30 (Amano). Subsequent conversion to the sulfide of high optical purity (approximately 95% e.e.) was accomplished by means of tri-n-butylphosphine and diphenyl disulfide. The alkylation of this difunctional intermediate with several electrophiles has proven to be rather impressively diastereoselective. The relative (and absolute) course of these transformations has been established by means of X-ray crystallographic and NMR methods and is rationalized at the mechanistic level.

  DOI：

  10.1016/s0957-4166(00)80137-8
• 作为产物：
  描述：

  氯甲基苯硫醚 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 苯亚硒酸 、 双氧水 、 三乙胺 、 zinc dibromide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 119.0h， 生成 (-)-3-methyl-2-<(phenylsulfonyl)methyl>butyl chloroacetate
  参考文献：
  名称：

  An enzyme-based synthesis of (S)-(−)-3-methyl-2-[(phenylsiilfonyl)-methyl]butyl phenyl sulfide and the stereochemical course of its alkylation

  摘要：

  The two title reactions have been explored. In the first instance, best results were achieved if the chloroacetate ester of 3-methyl-2[(phenylsulfonyl)methyl]-1-butanol was subjected to enzymatic hydrolysis with lipase P30 (Amano). Subsequent conversion to the sulfide of high optical purity (approximately 95% e.e.) was accomplished by means of tri-n-butylphosphine and diphenyl disulfide. The alkylation of this difunctional intermediate with several electrophiles has proven to be rather impressively diastereoselective. The relative (and absolute) course of these transformations has been established by means of X-ray crystallographic and NMR methods and is rationalized at the mechanistic level.

  DOI：

  10.1016/s0957-4166(00)80137-8

文献信息

• An enzyme-based synthesis of (S)-(−)-3-methyl-2-[(phenylsiilfonyl)-methyl]butyl phenyl sulfide and the stereochemical course of its alkylation
  作者：Ronan Guevel、Leo A. Paquette

  DOI：10.1016/s0957-4166(00)80137-8

  日期：1993.5

  The two title reactions have been explored. In the first instance, best results were achieved if the chloroacetate ester of 3-methyl-2[(phenylsulfonyl)methyl]-1-butanol was subjected to enzymatic hydrolysis with lipase P30 (Amano). Subsequent conversion to the sulfide of high optical purity (approximately 95% e.e.) was accomplished by means of tri-n-butylphosphine and diphenyl disulfide. The alkylation of this difunctional intermediate with several electrophiles has proven to be rather impressively diastereoselective. The relative (and absolute) course of these transformations has been established by means of X-ray crystallographic and NMR methods and is rationalized at the mechanistic level.