(4S)-4-benzyl-3-[2-(3-benzylimidazol-4-yl)acetyl]-1,3-oxazolidin-2-one | 186502-14-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S)-4-benzyl-3-[2-(3-benzylimidazol-4-yl)acetyl]-1,3-oxazolidin-2-one
• CAS: 186502-14-7
• 化学式: C₂₂H₂₁N₃O₃
• 分子量: 375.427
• InChiKey: WZJXCQGJQFHCGV-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  64.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S)-4-benzyl-3-[2-(3-benzylimidazol-4-yl)acetyl]-1,3-oxazolidin-2-one 在 咪唑 、 正丁基锂 、 MoO5*pyridine*HMPA 、 sodium hexamethyldisilazane 、 二异丁基氢化铝 、 溶剂黄146 、 苄硫醇 作用下， 反应 2.25h， 生成 (1S,2S)-1-(3-benzylimidazol-4-yl)-1-[tert-butyl(dimethyl)silyl]oxy-3-(methoxymethoxy)propan-2-ol
  参考文献：
  名称：

  A versatile, enantioselective, stereocontrolled synthesis of (1S,2R)-imidazoleglycerol

  摘要：

  An efficient (21% overall yield), enantio- and diastereoselective, 11-step synthesis of (1S,2R)-imidazoleglycerol has been developed. The key steps are the stereoselective hydroxylation of an acyloxazolidinone enolate, the alkylation of a thioester with (MOMOCH(2))(2)CuLi and the stereodivergent reduction of the resulting ketone. The scope of the reaction of the enolate derived from 10 with heteroatom electrophiles has been studied. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02138-7
• 作为产物：
  描述：

  1-苄基-5-(氯甲基)-1H-咪唑 在 氢氧化钾 、 sodium hydride 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4S)-4-benzyl-3-[2-(3-benzylimidazol-4-yl)acetyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  A versatile, enantioselective, stereocontrolled synthesis of (1S,2R)-imidazoleglycerol

  摘要：

  An efficient (21% overall yield), enantio- and diastereoselective, 11-step synthesis of (1S,2R)-imidazoleglycerol has been developed. The key steps are the stereoselective hydroxylation of an acyloxazolidinone enolate, the alkylation of a thioester with (MOMOCH(2))(2)CuLi and the stereodivergent reduction of the resulting ketone. The scope of the reaction of the enolate derived from 10 with heteroatom electrophiles has been studied. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02138-7

文献信息

• A versatile, enantioselective, stereocontrolled synthesis of (1S,2R)-imidazoleglycerol
  作者：Manuel M. Paz、Juan F. Cornea、M. Isabel Cabeza、F. Javier Sardina

  DOI：10.1016/s0040-4039(96)02138-7

  日期：1996.12

  An efficient (21% overall yield), enantio- and diastereoselective, 11-step synthesis of (1S,2R)-imidazoleglycerol has been developed. The key steps are the stereoselective hydroxylation of an acyloxazolidinone enolate, the alkylation of a thioester with (MOMOCH(2))(2)CuLi and the stereodivergent reduction of the resulting ketone. The scope of the reaction of the enolate derived from 10 with heteroatom electrophiles has been studied. Copyright (C) 1996 Elsevier Science Ltd