tert-butyl (2S,3S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-5-oxopyrrolidine-1-carboxylate | 1186233-61-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (2S,3S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-5-oxopyrrolidine-1-carboxylate
• CAS: 1186233-61-3
• 化学式: C₁₆H₃₁NO₅Si
• 分子量: 345.511
• InChiKey: YVJIPASVYCPFCF-RYUDHWBXSA-N

物化性质

• 沸点：
  426.6±30.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  tert-butyl (2S,3S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-5-oxopyrrolidine-1-carboxylate 在 咪唑 、 三苯基膦树脂 、 碘 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到tert-butyl (2R)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-5-oxo-2,5-dihydro-1H-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 tert-butyl (2S,3S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-5-oxopyrrolidine-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

文献信息

• Facile synthesis of unsaturated pyroglutaminol derivatives
  作者：Makoto Oba、Chihiro Ito、Takahiro Hayashi、Kozaburo Nishiyama

  DOI：10.1016/j.tetlet.2009.06.096

  日期：2009.9

  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.