methyl (2S,3S)-2-<(benzyloxy)carbonylamino>-3,4-epoxybutanoate | 117751-79-8

• 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 (2S,3S)-2-<(benzyloxy)carbonylamino>-3,4-epoxybutanoate
• 英文别名: 2(S)-methyl 2-N-benzyloxycarbonylamino-3,4-epoxybutanoate；Methyl (2S,3S)-2-<<(benzyloxy)carbonyl>amino>-3,4-epoxybutanoate；methyl (2S)-2-(benzyloxycarbonylamino)-2-[(2S)-oxiran-2-yl]acetate；methyl (2S)-2-[(2S)-oxiran-2-yl]-2-(phenylmethoxycarbonylamino)acetate
• CAS: 117751-79-8
• 化学式: C₁₃H₁₅NO₅
• 分子量: 265.266
• InChiKey: DHNFKFBAARYWOR-MNOVXSKESA-N

物化性质

• 沸点：
  427.1±30.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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-<(benzyloxy)carbonylamino>-3,4-epoxybutanoate 在 palladium on activated charcoal sodium azide 、 氢气 、 氯化铵 作用下， 以 甲醇 为溶剂， 反应 6.75h， 生成 Methyl (2S,3R)-4-azido-2-<(tert-butoxycarbonyl)amino>-3-hydroxybutanoate
  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
• 作为产物：
  描述：

  N-Cbz-L-蛋氨酸 在 sodium periodate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 xylene 为溶剂， 反应 38.0h， 生成 methyl (2S,3S)-2-<(benzyloxy)carbonylamino>-3,4-epoxybutanoate
  参考文献：
  名称：

  Fukuchi, Naoyuka; Isogai, Akira; Nakayama, Jiro, Journal of the Chemical Society. Perkin transactions I, 1992, # 9, p. 1149 - 1158

  摘要：

  DOI：

文献信息

• WO2020131807A5
  申请人：——

  公开号：WO2020131807A5

  公开（公告）日：2022-12-23
• 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
• 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.
• Fukuchi, Naoyuka; Isogai, Akira; Nakayama, Jiro, Journal of the Chemical Society. Perkin transactions I, 1992, # 9, p. 1149 - 1158
  作者：Fukuchi, Naoyuka、Isogai, Akira、Nakayama, Jiro、Takayama, Seiji、Yamashita, Shuichi、et al.

  DOI：——

  日期：——