Methanesulfonic acid (1S,3S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4,4,4-trifluoro-3-methanesulfonyloxymethyl-butyl ester | 1028271-14-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Methanesulfonic acid (1S,3S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4,4,4-trifluoro-3-methanesulfonyloxymethyl-butyl ester
• 英文别名: [(2S,4S)-5-[tert-butyl(dimethyl)silyl]oxy-4-methylsulfonyloxy-2-(trifluoromethyl)pentyl] methanesulfonate
• CAS: 1028271-14-8
• 化学式: C₁₄H₂₉F₃O₇S₂Si
• 分子量: 458.593
• InChiKey: XNMNJMXGIYEUJO-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (1S,3S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4,4,4-trifluoro-3-methanesulfonyloxymethyl-butyl ester 在 sodium sulfide 、 N,O-双三甲硅基乙酰胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 36.0h， 生成 (2'R)-L-N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethyl-4'-thiocytidine
  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 tetrahydroborate 、 氢气 作用下， 以 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 55.0 ℃ 、101.33 kPa 条件下， 反应 62.33h， 生成 Methanesulfonic acid (1S,3S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-4,4,4-trifluoro-3-methanesulfonyloxymethyl-butyl ester
  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.