Methyl (2S,3S)-2-<(tert-butoxycarbonyl)amino>-3,4-epoxybutanoate | 125229-18-7

• 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 (2S,3S)-2-<(tert-butoxycarbonyl)amino>-3,4-epoxybutanoate
• 英文别名: methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[(2S)-oxiran-2-yl]acetate
• CAS: 125229-18-7
• 化学式: C₁₀H₁₇NO₅
• 分子量: 231.249
• InChiKey: IBOSAGSAFPPUEU-RQJHMYQMSA-N

物化性质

• 沸点：
  335.0±17.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl (2S,3S)-2-<(tert-butoxycarbonyl)amino>-3,4-epoxybutanoate 在 高氯酸 作用下， 生成 (2S,3R)-3-Allyloxymethyl-1-(9-phenyl-9H-fluoren-9-yl)-aziridine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Enantiospecific synthesis of an aziridinobenzazocinone, an advanced intermediate containing the core nucleus of FR900482 and FK973

  摘要：

  DOI：

  10.1021/jo00291a010
• 作为产物：
  描述：

  (S)-2-(苄氧羰氨基)-3-丁烯酸甲酯 在 palladium on activated charcoal 氢气 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 Methyl (2S,3S)-2-<(tert-butoxycarbonyl)amino>-3,4-epoxybutanoate
  参考文献：
  名称：

  Chirospecific synthesis of the tetrahydroimidazodiazepinol aglycon of pentostatin and its analogs

  摘要：

  A high-yield, versatile method is presented for the stereo- and regiospecific synthesis of the aglycon of pentostatin and its analogues using the L-vinylglycine 1 as the chiral educt. From this four-carbon asymmetric core, containing the contiguous carbons of the target ring system, the synthetic process proceeds with development of the R absolute stereochemistry for the hydroxyl group at C-8 and nitrogen or potential nitrogen functions at the other three carbons. Conversion of the alpha-amino ester to an alpha-amino nitrile is followed by formation of the 1,4,5-trisubstituted aminoimidazole. After generating another amine by reduction of an azide, the diazepine is then annealed by treatment with orthoformate. Using this process, a series of (8R)-8-hydroxy-substituted tetrahydroimidazodiazepinols has been prepared. The protecting group protocol allows specific deprotection at N-3 for subsequent glycosylation and other substitution.

  DOI：

  10.1021/jo00074a041

文献信息

• Chirospecific synthesis of the tetrahydroimidazodiazepinol aglycon of pentostatin and its analogs
  作者：Thien Van Truong、Henry Rapoport

  DOI：10.1021/jo00074a041

  日期：1993.10

  A high-yield, versatile method is presented for the stereo- and regiospecific synthesis of the aglycon of pentostatin and its analogues using the L-vinylglycine 1 as the chiral educt. From this four-carbon asymmetric core, containing the contiguous carbons of the target ring system, the synthetic process proceeds with development of the R absolute stereochemistry for the hydroxyl group at C-8 and nitrogen or potential nitrogen functions at the other three carbons. Conversion of the alpha-amino ester to an alpha-amino nitrile is followed by formation of the 1,4,5-trisubstituted aminoimidazole. After generating another amine by reduction of an azide, the diazepine is then annealed by treatment with orthoformate. Using this process, a series of (8R)-8-hydroxy-substituted tetrahydroimidazodiazepinols has been prepared. The protecting group protocol allows specific deprotection at N-3 for subsequent glycosylation and other substitution.
• Enantiospecific synthesis of an aziridinobenzazocinone, an advanced intermediate containing the core nucleus of FR900482 and FK973
  作者：Robert J. Jones、Henry Rapoport

  DOI：10.1021/jo00291a010

  日期：1990.2