(4S,5S)-4-Allyl-5-benzyloxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | 365449-53-2

• 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)-4-Allyl-5-benzyloxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S,5S)-2,2-dimethyl-5-(phenylmethoxymethyl)-4-prop-2-enyl-1,3-oxazolidine-3-carboxylate
• CAS: 365449-53-2
• 化学式: C₂₁H₃₁NO₄
• 分子量: 361.481
• InChiKey: OOYYNOPGYDDGAV-ZWKOTPCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-Allyl-5-benzyloxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 草酰氯 、 氨 、 四丁基碘化铵 、 lithium 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.08h， 生成 (4S,5S)-4-Allyl-5-((S)-benzyloxy-thiazol-2-yl-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
• 作为产物：
  描述：

  在 sodium hydroxide 、 对甲苯磺酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (4S,5S)-4-Allyl-5-benzyloxymethyl-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.