tert-Butyl-dimethyl-((2R,4S)-1-oxo-4-trifluoromethyl-tetrahydro-1λ⁴-thiophen-2-ylmethoxy)-silane | 1027033-81-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环戊烷
• 英文名称: tert-Butyl-dimethyl-((2R,4S)-1-oxo-4-trifluoromethyl-tetrahydro-1λ⁴-thiophen-2-ylmethoxy)-silane
• 英文别名: tert-butyl-dimethyl-[[(2R,4S)-1-oxo-4-(trifluoromethyl)thiolan-2-yl]methoxy]silane
• CAS: 1027033-81-3
• 化学式: C₁₂H₂₃F₃O₂SSi
• 分子量: 316.46
• InChiKey: IXUKNXFCNVTEQK-IHOZLYAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 tert-Butyl-dimethyl-((2R,4S)-1-oxo-4-trifluoromethyl-tetrahydro-1λ⁴-thiophen-2-ylmethoxy)-silane 反应 4.5h， 以137 mg的产率得到(3S,5R)-5-(tert-butyldimethyl-silanoxymethyl)-3-trifluoromethyl-tetrahydrothiophen-2-yl acetate
  参考文献：
  名称：

  Synthesis of Novel l-2‘,3‘-Dideoxy-2‘-trifluoromethyl-4‘- thiocytidines from α-Trifluoromethyl-α,β-unsaturated Ester

  摘要：

  A short and efficient synthesis of L-2',3'-dideoxy-2 -trifluoromethyl-4'-thiocytidines is described. (2R,4S/2S,4S)5-(tert-Butyldimethylsiloxy)-2-trifluoromethylpentan-4- olide (3a and 3b) are prepared from alpha-trifluoromethyl-alpha,beta-unsaturated ester (1) in three steps and converted to compounds 6a and 6b. The corresponding 1-O-acetyl derivatives 8a and 8b were obtained via the usual Pummerer rearrangement from 6a and 6b in two steps, which were in turn used to synthesize L-4'-thiocytidines 10a and 10b.

  DOI：

  10.1021/jo0159690
• 作为产物：
  描述：

  (Z)/(E)-ethyl 3-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-trifluoromethyl-2-propenoate 在 10percent Pd/C 咪唑 、 盐酸 、 sodium sulfide 、 sodium tetrahydroborate 、 氢气 、 间氯过氧苯甲酸 作用下， 以 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -78.0~100.0 ℃ 、101.33 kPa 条件下， 反应 69.33h， 生成 tert-Butyl-dimethyl-((2R,4S)-1-oxo-4-trifluoromethyl-tetrahydro-1λ⁴-thiophen-2-ylmethoxy)-silane
  参考文献：
  名称：

  Synthesis of Novel l-2‘,3‘-Dideoxy-2‘-trifluoromethyl-4‘- thiocytidines from α-Trifluoromethyl-α,β-unsaturated Ester

  摘要：

  A short and efficient synthesis of L-2',3'-dideoxy-2 -trifluoromethyl-4'-thiocytidines is described. (2R,4S/2S,4S)5-(tert-Butyldimethylsiloxy)-2-trifluoromethylpentan-4- olide (3a and 3b) are prepared from alpha-trifluoromethyl-alpha,beta-unsaturated ester (1) in three steps and converted to compounds 6a and 6b. The corresponding 1-O-acetyl derivatives 8a and 8b were obtained via the usual Pummerer rearrangement from 6a and 6b in two steps, which were in turn used to synthesize L-4'-thiocytidines 10a and 10b.

  DOI：

  10.1021/jo0159690

文献信息

• Synthesis of Novel <scp>l</scp>-2‘,3‘-Dideoxy-2‘-trifluoromethyl-4‘- thiocytidines from <i>α</i>-Trifluoromethyl-<i>α</i>,<i>β</i>-unsaturated Ester
  作者：Xingang Zhang、Feng-Ling Qing

  DOI：10.1021/jo0159690

  日期：2002.2.1

  A short and efficient synthesis of L-2',3'-dideoxy-2 -trifluoromethyl-4'-thiocytidines is described. (2R,4S/2S,4S)5-(tert-Butyldimethylsiloxy)-2-trifluoromethylpentan-4- olide (3a and 3b) are prepared from alpha-trifluoromethyl-alpha,beta-unsaturated ester (1) in three steps and converted to compounds 6a and 6b. The corresponding 1-O-acetyl derivatives 8a and 8b were obtained via the usual Pummerer rearrangement from 6a and 6b in two steps, which were in turn used to synthesize L-4'-thiocytidines 10a and 10b.