(4S,5S)-5-benzyloxymethyl-4-hydroxy-1-t-butoxycarbonylpyrrolidin-2-one | 112700-47-7

• 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: (4S,5S)-5-benzyloxymethyl-4-hydroxy-1-t-butoxycarbonylpyrrolidin-2-one
• 英文别名: tert-butyl (2S,3S)-3-hydroxy-5-oxo-2-(phenylmethoxymethyl)pyrrolidine-1-carboxylate
• CAS: 112700-47-7
• 化学式: C₁₇H₂₃NO₅
• 分子量: 321.373
• InChiKey: IVQAHEINPAZNOT-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5S)-5-benzyloxymethyl-4-hydroxy-1-t-butoxycarbonylpyrrolidin-2-one 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到tert-butyl (2R)-5-oxo-2-(phenylmethoxymethyl)-2H-pyrrole-1-carboxylate
  参考文献：
  名称：

  Facile synthesis of unsaturated pyroglutaminol derivatives

  摘要：

  A novel approach to the synthesis of unsaturated pyroglutaminol derivatives was developed. Condensation of a protected serine derivative with Meldrum's acid followed by decarboxylative cyclization afforded a tetramic acid, which was then converted to a hydroxylactam using sodium borohydride. Iodine displacement of the hydroxyl group induced spontaneous elimination to afford unsaturated pyroglutaminol derivatives in good yields. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.096
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 二氯甲烷 为溶剂， 生成 (4S,5S)-5-benzyloxymethyl-4-hydroxy-1-t-butoxycarbonylpyrrolidin-2-one
  参考文献：
  名称：

  Facile synthesis of unsaturated pyroglutaminol derivatives

  摘要：

  A novel approach to the synthesis of unsaturated pyroglutaminol derivatives was developed. Condensation of a protected serine derivative with Meldrum's acid followed by decarboxylative cyclization afforded a tetramic acid, which was then converted to a hydroxylactam using sodium borohydride. Iodine displacement of the hydroxyl group induced spontaneous elimination to afford unsaturated pyroglutaminol derivatives in good yields. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.06.096

文献信息

• Jouin, Patrick; Castro, Bertrand; Nisato, Dino, Journal of the Chemical Society. Perkin transactions I, 1987, p. 1177 - 1182
  作者：Jouin, Patrick、Castro, Bertrand、Nisato, Dino

  DOI：——

  日期：——
• JOUIN, PATRICK;CASTRO, BERTRAND, J. CHEM. SOC. PERKIN TRANS., PT 1,(1987) N 6, 1177-1182
  作者：JOUIN, PATRICK、CASTRO, BERTRAND

  DOI：——

  日期：——