(4S,5S)-4-Allyl-5-((S)-benzyloxy-carboxy-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | 365449-52-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5S)-4-Allyl-5-((S)-benzyloxy-carboxy-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: (2S)-2-[(4S,5S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-4-prop-2-enyl-1,3-oxazolidin-5-yl]-2-phenylmethoxyacetic acid
• CAS: 365449-52-1
• 化学式: C₂₂H₃₁NO₆
• 分子量: 405.491
• InChiKey: FTPDKMUHEPYUOO-BZSNNMDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-Allyl-5-((S)-benzyloxy-carboxy-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 4-二甲氨基吡啶 、 臭氧 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (4S,5S)-5-{(S)-Benzyloxy-[(S)-1-((S)-8-methoxy-1-oxo-isochroman-3-yl)-3-methyl-butylcarbamoyl]-methyl}-2,2-dimethyl-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Pseudopeptide Microbial Agent AI-77-B

  摘要：

  [GRAPHICS]An efficient and highly stereoselective synthesis of the gastroprotective natural product Al-77-B is described. The stereocenters of the hydroxy amino acid moiety were generated by an ester-derived titanium-enolate-mediated syn-aldol reaction, a Curtius rearrangement, and application of Dondoni's aldehyde homologation. Condensation with the dihydroisocoumarin fragment and subsequent deprotecting transformations furnished optically active Al-77-B.

  DOI：

  10.1021/ol0101279
• 作为产物：
  描述：

  (4S,5S)-4-Allyl-5-((S)-1-benzyloxy-2-oxo-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 水 、 叔丁醇 为溶剂， 以98%的产率得到(4S,5S)-4-Allyl-5-((S)-benzyloxy-carboxy-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Pseudopeptide Microbial Agent AI-77-B

  摘要：

  [GRAPHICS]An efficient and highly stereoselective synthesis of the gastroprotective natural product Al-77-B is described. The stereocenters of the hydroxy amino acid moiety were generated by an ester-derived titanium-enolate-mediated syn-aldol reaction, a Curtius rearrangement, and application of Dondoni's aldehyde homologation. Condensation with the dihydroisocoumarin fragment and subsequent deprotecting transformations furnished optically active Al-77-B.

  DOI：

  10.1021/ol0101279

文献信息

• Stereoselective Synthesis of Pseudopeptide Microbial Agent AI-77-B
  作者：Arun K. Ghosh、Alexander Bischoff、John Cappiello

  DOI：10.1021/ol0101279

  日期：2001.8.1

  [GRAPHICS]An efficient and highly stereoselective synthesis of the gastroprotective natural product Al-77-B is described. The stereocenters of the hydroxy amino acid moiety were generated by an ester-derived titanium-enolate-mediated syn-aldol reaction, a Curtius rearrangement, and application of Dondoni's aldehyde homologation. Condensation with the dihydroisocoumarin fragment and subsequent deprotecting transformations furnished optically active Al-77-B.