[(3R,4R)-4-benzylsulfanyl-1,1-dioxothiolan-3-yl] acetate | 908026-53-9

• 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: [(3R,4R)-4-benzylsulfanyl-1,1-dioxothiolan-3-yl] acetate
• CAS: 908026-53-9
• 化学式: C₁₃H₁₆O₄S₂
• 分子量: 300.4
• InChiKey: DEKLATVDQIOPCP-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  94.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(3R,4R)-4-benzylsulfanyl-1,1-dioxothiolan-3-yl] acetate 在 sodium periodate 作用下， 以 乙醇 为溶剂， 以88%的产率得到[(3S)-1,1-dioxo-2,3-dihydrothiophen-3-yl] acetate
  参考文献：
  名称：

  Enzymatic kinetic resolution of 1,1-dioxo-2,3-dihydro-1H-1λ6-thiophen-3-ol via temporary derivatisation

  摘要：

  Following the thio-conjugate addition of (+/-)-9, its enantiomers were extremely efficiently discriminated using Novozym 435 (R). The thio-differentiating unit may then be removed either under reductive conditions, using Raney nickel, or following an oxidation-elimination sequence. In this manner enantioenriched derivatives of 1,1-dioxo-2,3-dihydro-1H-1 lambda(6)-thiophen-3-ol 9 may be accessed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.153
• 作为产物：
  描述：

  (3R,4R)-4-benzylsulfanyl-1,1-dioxothiolan-3-ol 、 乙酸乙烯酯 在 Novozym 435(R) 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以46%的产率得到(3S,4S)-4-benzylsulfanyl-1,1-dioxothiolan-3-ol
  参考文献：
  名称：

  Enzymatic kinetic resolution of 1,1-dioxo-2,3-dihydro-1H-1λ6-thiophen-3-ol via temporary derivatisation

  摘要：

  Following the thio-conjugate addition of (+/-)-9, its enantiomers were extremely efficiently discriminated using Novozym 435 (R). The thio-differentiating unit may then be removed either under reductive conditions, using Raney nickel, or following an oxidation-elimination sequence. In this manner enantioenriched derivatives of 1,1-dioxo-2,3-dihydro-1H-1 lambda(6)-thiophen-3-ol 9 may be accessed. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.153