Methyl-{(S)-1-methyl-2-oxo-2-[(4S,5S)-2,2,4-trimethyl-5-((S)-1-methyl-allyl)-oxazolidin-3-yl]-ethyl}-carbamic acid tert-butyl ester | 289622-58-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Methyl-{(S)-1-methyl-2-oxo-2-[(4S,5S)-2,2,4-trimethyl-5-((S)-1-methyl-allyl)-oxazolidin-3-yl]-ethyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S)-1-[(4S,5S)-5-[(2S)-but-3-en-2-yl]-2,2,4-trimethyl-1,3-oxazolidin-3-yl]-1-oxopropan-2-yl]-N-methylcarbamate
• CAS: 289622-58-8
• 化学式: C₁₉H₃₄N₂O₄
• 分子量: 354.49
• InChiKey: QNSUKYKGILVFMK-AJNGGQMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl-{(S)-1-methyl-2-oxo-2-[(4S,5S)-2,2,4-trimethyl-5-((S)-1-methyl-allyl)-oxazolidin-3-yl]-ethyl}-carbamic acid tert-butyl ester 在 ruthenium trichloride sodium periodate 作用下， 以78%的产率得到(R)-2-{(4S,5S)-3-[(S)-2-(tert-Butoxycarbonyl-methyl-amino)-propionyl]-2,2,4-trimethyl-oxazolidin-5-yl}-propionic acid
  参考文献：
  名称：

  Stereochemistry and total synthesis of janolusimide, a tripeptide marine toxin

  摘要：

  The stereochemistry of janolusimide, a lipophilic tripeptide marine toxin, has been fully elucidated by stereoselective synthesis of the lactam component (5S)-3,3'-dimethyl-5-isopropylpyrrolidin-2,4-dione. The peptide was then synthesized in 13 steps and in 0.8% total yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00533-5
• 作为产物：
  描述：

  ((1S,2S,3S)-2-Hydroxy-1,3-dimethyl-pent-4-enyl)-carbamic acid tert-butyl ester 在 盐酸 、 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 生成 Methyl-{(S)-1-methyl-2-oxo-2-[(4S,5S)-2,2,4-trimethyl-5-((S)-1-methyl-allyl)-oxazolidin-3-yl]-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Stereochemistry and total synthesis of janolusimide, a tripeptide marine toxin

  摘要：

  The stereochemistry of janolusimide, a lipophilic tripeptide marine toxin, has been fully elucidated by stereoselective synthesis of the lactam component (5S)-3,3'-dimethyl-5-isopropylpyrrolidin-2,4-dione. The peptide was then synthesized in 13 steps and in 0.8% total yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00533-5

文献信息

• Stereochemistry and total synthesis of janolusimide, a tripeptide marine toxin
  作者：Assunta Giordano、Carmela Della Monica、Francesco Landi、Aldo Spinella、Guido Sodano

  DOI：10.1016/s0040-4039(00)00533-5

  日期：2000.5

  The stereochemistry of janolusimide, a lipophilic tripeptide marine toxin, has been fully elucidated by stereoselective synthesis of the lactam component (5S)-3,3'-dimethyl-5-isopropylpyrrolidin-2,4-dione. The peptide was then synthesized in 13 steps and in 0.8% total yield. (C) 2000 Elsevier Science Ltd. All rights reserved.