(2R,5R)-1-tert-butoxycarbonyl-2-tert-butyldimethylsilyloxymethyl-5-benzyloxymethylpyrrolidine | 253776-48-6

• 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: (2R,5R)-1-tert-butoxycarbonyl-2-tert-butyldimethylsilyloxymethyl-5-benzyloxymethylpyrrolidine
• 英文别名: tert-butyl (2S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(phenylmethoxymethyl)pyrrolidine-1-carboxylate
• CAS: 253776-48-6
• 化学式: C₂₄H₄₁NO₄Si
• 分子量: 435.679
• InChiKey: DQIZCTARQWEGIZ-RTWAWAEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.99
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 (2R,5R)-1-tert-butoxycarbonyl-2-tert-butyldimethylsilyloxymethyl-5-benzyloxymethylpyrrolidine 反应 4.0h， 生成 (2R,5R)-2-hydroxymethyl-5-benzyloxymethylpyrrolidine trifluoroacetate
  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
• 作为产物：
  描述：

  (S)-(-)-3-苄氧基-1,2-丙二醇 在 吡啶 、 disodium hydrogenphosphate 、 正丁基锂 、 sodium amalgam 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.33h， 生成 (2R,5R)-1-tert-butoxycarbonyl-2-tert-butyldimethylsilyloxymethyl-5-benzyloxymethylpyrrolidine
  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