(4S,5S)-4-Allyl-5-((S)-benzyloxy-thiazol-2-yl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | 365449-61-2

• 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-((S)-benzyloxy-thiazol-2-yl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S,5S)-2,2-dimethyl-5-[(S)-phenylmethoxy(1,3-thiazol-2-yl)methyl]-4-prop-2-enyl-1,3-oxazolidine-3-carboxylate
• CAS: 365449-61-2
• 化学式: C₂₄H₃₂N₂O₄S
• 分子量: 444.595
• InChiKey: KQFYJNYWMPRSRL-UFYCRDLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  三氟甲烷磺酸甲酯 、 (4S,5S)-4-Allyl-5-((S)-benzyloxy-thiazol-2-yl-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 4 A molecular sieve 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成
  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-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 草酰氯 、 四丁基碘化铵 、 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 18.0h， 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

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.