(2'S)-L-N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethyl-4'-thiocytidine | 402757-25-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (2'S)-L-N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethyl-4'-thiocytidine
• 英文别名: N-[1-[(2S,3S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(trifluoromethyl)thiolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 402757-25-9
• 化学式: C₂₃H₃₀F₃N₃O₃SSi
• 分子量: 513.656
• InChiKey: WBBCMXOYRRZMGW-HLIPFELVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  96.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2'S)-L-N⁴-benzoyl-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-2'-trifluoromethyl-4'-thiocytidine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 N-[1-((2S,3S,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：

  N4-苯甲酰基胞嘧啶 、 (3S,5R)-5-(tert-butyldimethyl-silanoxymethyl)-3-trifluoromethyl-tetrahydrothiophen-2-yl acetate 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 24.5h， 以141 mg的产率得到(2'S)-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

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.