(4R,5S)-3-benzyl-5-((1S)-2-O-carbamoyl-1-benzyloxyethyl)-4-vinyl-1,3-oxazolan-2-one | 949490-41-9

• 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: (4R,5S)-3-benzyl-5-((1S)-2-O-carbamoyl-1-benzyloxyethyl)-4-vinyl-1,3-oxazolan-2-one
• 英文别名: [(2S)-2-[(4R,5S)-3-benzyl-4-ethenyl-2-oxo-1,3-oxazolidin-5-yl]-2-phenylmethoxyethyl] carbamate
• CAS: 949490-41-9
• 化学式: C₂₂H₂₄N₂O₅
• 分子量: 396.443
• InChiKey: LGXIDSLXGRSFTN-AABGKKOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  91.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5S)-3-benzyl-5-((1S)-2-O-carbamoyl-1-benzyloxyethyl)-4-vinyl-1,3-oxazolan-2-one 在 臭氧 、 双氧水 作用下， 以 乙酸乙酯 、 水 为溶剂， 反应 0.08h， 以30%的产率得到(2S,3S,4S)-2-benzyloxy-3-O,4-N-benzyl-carbamate-1-aminocarbonyloxypentanoic acid
  参考文献：
  名称：

  New approach to carbamoyl-polyoxamic acid derivatives through an oxazolidinone synthon

  摘要：

  A key oxazolidinone synthon was obtained through condensation of vinyl magnesium with an epoxyimine, followed by a carbonation/cyclisation reaction in the presence of ammonium carbonate. Oxidative ozonolysis after protection and carbamolylation (optional) afforded the (5-0-carbamoyl-)polyoxamic derivatives in 9% (or 14%) total yield in six (or four) steps. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.06.002
• 作为产物：
  描述：

  (1R)-N-benzyl-1-[(2R,3S)-3-[[tert-butyl(diphenyl)silyl]oxymethyl]oxiran-2-yl]prop-2-en-1-amine 在 吡啶 、 四丁基氟化铵 、 silica gel 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 29.0h， 生成 (4R,5S)-3-benzyl-5-((1S)-2-O-carbamoyl-1-benzyloxyethyl)-4-vinyl-1,3-oxazolan-2-one
  参考文献：
  名称：

  New approach to carbamoyl-polyoxamic acid derivatives through an oxazolidinone synthon

  摘要：

  A key oxazolidinone synthon was obtained through condensation of vinyl magnesium with an epoxyimine, followed by a carbonation/cyclisation reaction in the presence of ammonium carbonate. Oxidative ozonolysis after protection and carbamolylation (optional) afforded the (5-0-carbamoyl-)polyoxamic derivatives in 9% (or 14%) total yield in six (or four) steps. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.06.002

文献信息

• New approach to carbamoyl-polyoxamic acid derivatives through an oxazolidinone synthon
  作者：Magalie Collet、Yves Génisson、Michel Baltas

  DOI：10.1016/j.tetasy.2007.06.002

  日期：2007.6

  A key oxazolidinone synthon was obtained through condensation of vinyl magnesium with an epoxyimine, followed by a carbonation/cyclisation reaction in the presence of ammonium carbonate. Oxidative ozonolysis after protection and carbamolylation (optional) afforded the (5-0-carbamoyl-)polyoxamic derivatives in 9% (or 14%) total yield in six (or four) steps. (c) 2007 Elsevier Ltd. All rights reserved.