(2S)-1-O-benzylglycerol-2,3-bis(trifluoromethanesulfonate) | 253776-34-0

• 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: (2S)-1-O-benzylglycerol-2,3-bis(trifluoromethanesulfonate)
• 英文别名: (2S)-1-O-benzylglycerol-2,3-bistriflate；[(2S)-3-phenylmethoxy-2-(trifluoromethylsulfonyloxy)propyl] trifluoromethanesulfonate
• CAS: 253776-34-0
• 化学式: C₁₂H₁₂F₆O₇S₂
• 分子量: 446.345
• InChiKey: DJUCHPVZEYKERQ-JTQLQIEISA-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：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (2S)-1-O-benzylglycerol-2,3-bis(trifluoromethanesulfonate) 在 disodium hydrogenphosphate 、 正丁基锂 、 sodium amalgam 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 25.5h， 生成 (2S,5R)-1-tert-butoxycarbonyl-5-hydroxymethyl-2-benzyloxymethyl pyrrolidine
  参考文献：
  名称：

  Facile synthesis of N-Boc-(2S,5R)-5-(1′-hydroxy-1′-methylethyl)proline

  摘要：

  Coupling of chiral 1-O-benzylglycerol-2,3-bistriflate with trilithiated chiral 2-N-Boc-3-phenylsulfonylpropan-1-ol derivative constitutes an efficient route to chiral C-5 substituted prolines which can potentially induce cis Xaa-Pro peptide bond conformation. A straightforward seven-step synthesis of the title compound is described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00537-3
• 作为产物：
  描述：

  三氟甲磺酸酐 、 (R)-(+)-3-苄氧基-1,2-丙二醇 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以95%的产率得到(2S)-1-O-benzylglycerol-2,3-bis(trifluoromethanesulfonate)
  参考文献：
  名称：

  A Versatile Method for the Facile Synthesis of Enantiopure trans- and cis-2,5-Disubstituted Pyrrolidines

  摘要：

  Treatment of(2S)-1-O-benzylglycerol-2,3-bistrifiate (2) with the trilithiated species of chiral building blocks 5-7 provided 2,3,5-trisubstituted pyrrolidines that were subjected to reductive desulfonylation to give trans-2,5-disubstituted pyrrolidines 11-13, respectively. The same reaction sequence with the (2R)-bistriflate 4 and trilithiated 5 afforded the cia isomer 19. This two-step synthetic mehodology can furnish any one of the four possible diastereomers of enantiopure 2,5-disubstituted pyrrolidines in 60-72% overall yields.

  DOI：

  10.1021/jo991052d

文献信息

• Facile synthesis of N-Boc-(2S,5R)-5-(1′-hydroxy-1′-methylethyl)proline
  作者：Qian Wang、Marie-Elise Tran Huu Dau、N André Sasaki、Pierre Potier

  DOI：10.1016/s0040-4020(01)00537-3

  日期：2001.7

  Coupling of chiral 1-O-benzylglycerol-2,3-bistriflate with trilithiated chiral 2-N-Boc-3-phenylsulfonylpropan-1-ol derivative constitutes an efficient route to chiral C-5 substituted prolines which can potentially induce cis Xaa-Pro peptide bond conformation. A straightforward seven-step synthesis of the title compound is described. (C) 2001 Elsevier Science Ltd. All rights reserved.
• A Versatile Method for the Facile Synthesis of Enantiopure <i>trans-</i> and <i>cis</i>-2,5-Disubstituted Pyrrolidines
  作者：Qian Wang、N. André Sasaki、Claude Riche、Pierre Potier

  DOI：10.1021/jo991052d

  日期：1999.11.1

  Treatment of(2S)-1-O-benzylglycerol-2,3-bistrifiate (2) with the trilithiated species of chiral building blocks 5-7 provided 2,3,5-trisubstituted pyrrolidines that were subjected to reductive desulfonylation to give trans-2,5-disubstituted pyrrolidines 11-13, respectively. The same reaction sequence with the (2R)-bistriflate 4 and trilithiated 5 afforded the cia isomer 19. This two-step synthetic mehodology can furnish any one of the four possible diastereomers of enantiopure 2,5-disubstituted pyrrolidines in 60-72% overall yields.