((S)-2-{(4S,5S)-5-[(R)-2-((R)-5-Isopropyl-3,3-dimethyl-2,4-dioxo-pyrrolidin-1-yl)-1-methyl-2-oxo-ethyl]-2,2,4-trimethyl-oxazolidin-3-yl}-1-methyl-2-oxo-ethyl)-methyl-carbamic acid tert-butyl ester | 289622-63-5

• 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: ((S)-2-{(4S,5S)-5-[(R)-2-((R)-5-Isopropyl-3,3-dimethyl-2,4-dioxo-pyrrolidin-1-yl)-1-methyl-2-oxo-ethyl]-2,2,4-trimethyl-oxazolidin-3-yl}-1-methyl-2-oxo-ethyl)-methyl-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S)-1-[(4S,5S)-5-[(2R)-1-[(5R)-3,3-dimethyl-2,4-dioxo-5-propan-2-ylpyrrolidin-1-yl]-1-oxopropan-2-yl]-2,2,4-trimethyl-1,3-oxazolidin-3-yl]-1-oxopropan-2-yl]-N-methylcarbamate
• CAS: 289622-63-5
• 化学式: C₂₇H₄₅N₃O₇
• 分子量: 523.67
• InChiKey: HTRWEACYVDFVIE-SPOLIRPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ((S)-2-{(4S,5S)-5-[(R)-2-((R)-5-Isopropyl-3,3-dimethyl-2,4-dioxo-pyrrolidin-1-yl)-1-methyl-2-oxo-ethyl]-2,2,4-trimethyl-oxazolidin-3-yl}-1-methyl-2-oxo-ethyl)-methyl-carbamic acid tert-butyl ester 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 (S)-N-[(1S,2S,3R)-2-Hydroxy-4-((R)-5-isopropyl-3,3-dimethyl-2,4-dioxo-pyrrolidin-1-yl)-1,3-dimethyl-4-oxo-butyl]-2-methylamino-propionamide
  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：

  ethyl (4S)-2,2,5-trimethyl-3-oxo-4-(phenylmethoxycarbonylamino)hexanoate 在 palladium on activated charcoal sodium tetrahydroborate 、 重铬酸吡啶 、 正丁基锂 、 molecular sieve 、 氢气 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 ((S)-2-{(4S,5S)-5-[(R)-2-((R)-5-Isopropyl-3,3-dimethyl-2,4-dioxo-pyrrolidin-1-yl)-1-methyl-2-oxo-ethyl]-2,2,4-trimethyl-oxazolidin-3-yl}-1-methyl-2-oxo-ethyl)-methyl-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