(3R,5R)-5-(tert-butyldimethyl-silanoxymethyl)-3-trifluoromethyl-tetrahydrothiophen-2-yl acetate | 402757-22-6

• 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: (3R,5R)-5-(tert-butyldimethyl-silanoxymethyl)-3-trifluoromethyl-tetrahydrothiophen-2-yl acetate
• 英文别名: [(3R,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(trifluoromethyl)thiolan-2-yl] acetate
• CAS: 402757-22-6
• 化学式: C₁₄H₂₅F₃O₃SSi
• 分子量: 358.497
• InChiKey: PNTGKQBEJBFFJK-UBNQGINQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R,5R)-5-(tert-butyldimethyl-silanoxymethyl)-3-trifluoromethyl-tetrahydrothiophen-2-yl acetate 在 N,O-双三甲硅基乙酰胺 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 25.5h， 生成 N-[1-((2S,3R,5R)-5-Hydroxymethyl-3-trifluoromethyl-tetrahydro-thiophen-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide
  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 73.83h， 生成 (3R,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