(2R,3S)-2-((R)-3-Acetylsulfanyl-2-tert-butoxycarbonylamino-propionylamino)-3-hydroxy-butyric acid methyl ester | 159418-64-1

• 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: (2R,3S)-2-((R)-3-Acetylsulfanyl-2-tert-butoxycarbonylamino-propionylamino)-3-hydroxy-butyric acid methyl ester
• 英文别名: Boc-Cys(Ac)-D-Thr-OMe；methyl (2R,3S)-2-[[(2R)-3-acetylsulfanyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-3-hydroxybutanoate
• CAS: 159418-64-1
• 化学式: C₁₅H₂₆N₂O₇S
• 分子量: 378.447
• InChiKey: QGMJFGQCBBAZLM-INTQDDNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  156
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-((R)-3-Acetylsulfanyl-2-tert-butoxycarbonylamino-propionylamino)-3-hydroxy-butyric acid methyl ester 在 Lithium-tri-methoxy-alanat 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2S,3S,6R)-6-tert-butoxycarbonylamino-3-methoxycarbonyl-2-methyl-5-oxoperhydro-1,4-thiazepine
  参考文献：
  名称：

  Cyclic dipeptides. A stereocontrolled synthesis of (2S,3R,6R)- and (2R,3R,6R)-6-tert-butoxycarbonylamino-3-methoxycarbonyl-2-methyl-5-oxoperhydro-1,4-thiazepine

  摘要：

  A stereselective synthesis of the title compounds, starting from commercially available amino acids, is described. The absolute stereochemistry of 3a and 3b has been deduced on the basis of H-1 NMR and chemical degradation studies. The formation of only these two isomers has been rationalized in terms of molecular mechanics calculations.

  DOI：

  10.1016/0957-4166(94)80115-0
• 作为产物：
  描述：

  Z-苏氨酸甲酯 、 S-Ac-N-Boc-L-Cys 在 N-cyclohexyl-N'-(2-morpholinoethyl)carbodiimide methyl p-toluenesulfonate 作用下， 以 二氯甲烷 为溶剂， 以53%的产率得到(2R,3S)-2-((R)-3-Acetylsulfanyl-2-tert-butoxycarbonylamino-propionylamino)-3-hydroxy-butyric acid methyl ester
  参考文献：
  名称：

  Cyclic dipeptides. A stereocontrolled synthesis of (2S,3R,6R)- and (2R,3R,6R)-6-tert-butoxycarbonylamino-3-methoxycarbonyl-2-methyl-5-oxoperhydro-1,4-thiazepine

  摘要：

  A stereselective synthesis of the title compounds, starting from commercially available amino acids, is described. The absolute stereochemistry of 3a and 3b has been deduced on the basis of H-1 NMR and chemical degradation studies. The formation of only these two isomers has been rationalized in terms of molecular mechanics calculations.

  DOI：

  10.1016/0957-4166(94)80115-0

文献信息

• Cyclic dipeptides. A stereocontrolled synthesis of (2S,3R,6R)- and (2R,3R,6R)-6-tert-butoxycarbonylamino-3-methoxycarbonyl-2-methyl-5-oxoperhydro-1,4-thiazepine
  作者：Federico Corelli、Angela Crescenza、Donata Dei、Maurizio Taddei、Maurizio Botta

  DOI：10.1016/0957-4166(94)80115-0

  日期：1994.8

  A stereselective synthesis of the title compounds, starting from commercially available amino acids, is described. The absolute stereochemistry of 3a and 3b has been deduced on the basis of H-1 NMR and chemical degradation studies. The formation of only these two isomers has been rationalized in terms of molecular mechanics calculations.