(2S,3R)-2-Amino-4-azido-3-<(tert-butyldimethylsilyl)oxy>butyronitrile | 151256-24-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,3R)-2-Amino-4-azido-3-<(tert-butyldimethylsilyl)oxy>butyronitrile
• 英文别名: (2R,3R)-2-amino-4-azido-3-[tert-butyl(dimethyl)silyl]oxybutanenitrile
• CAS: 151256-24-5
• 化学式: C₁₀H₂₁N₅OSi
• 分子量: 255.395
• InChiKey: YATDPNXWLBRGGM-RKDXNWHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  73.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-Amino-4-azido-3-<(tert-butyldimethylsilyl)oxy>butyronitrile 在 5A molecular sieve 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 5-Amino-4-<(1'R)-<(2'-azido-1'-tert-butyldimethylsilyl)oxy>ethyl>-1-(2'-cyanoethyl)imidazole
  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：

  (2S,3R)-4-Azido-2-<(tert-butoxycarbonyl)amino>-3-<(tert-butyldimethylsilyl)oxy>butyronitrile 在 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.75h， 以93%的产率得到(2S,3R)-2-Amino-4-azido-3-<(tert-butyldimethylsilyl)oxy>butyronitrile
  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

• Enantiospecific Synthesis of Carbapentostatins
  作者：Jonathan Z. Ho、Rafat M. Mohareb、Jin Hee Ahn、Tae Bo Sim、Henry Rapoport

  DOI：10.1021/jo020612x

  日期：2003.1.1

  In this paper we describe enantioselective syntheses of (+)-carbapentostatin (8) and its cyclopentyl analogue 12b. A new and efficient one-pot, two-step preparation of aldehyde 15 has been developed, based on the borane reduction of N-Pf-protected L-aspartic acid gamma-methyl ester (13) and Swern, oxidation of the resulting alcohol. Homologation to diester 18 and ring formation by Dieckman cyclization, followed by reduction and dehydration steps, afford the 4-amino-1-cyclopentenemethanol derivative 22. Hydroboration and oxidation transform this compound stereospecifically into aminocyclopentanol 26, the key aminocyclitol component for an asymmetric synthesis of (+)carbapentostatin.
• 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.