5-[(R)-2-Azido-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-cyclopentyl-3H-imidazol-4-ylamine | 493038-97-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-[(R)-2-Azido-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-cyclopentyl-3H-imidazol-4-ylamine
• 英文别名: 5-[(1R)-2-azido-1-[tert-butyl(dimethyl)silyl]oxyethyl]-3-cyclopentylimidazol-4-amine
• CAS: 493038-97-4
• 化学式: C₁₆H₃₀N₆OSi
• 分子量: 350.539
• InChiKey: CREZXGADHCSUJO-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  24
• 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：
  67.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[(R)-2-Azido-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-cyclopentyl-3H-imidazol-4-ylamine 在 1,3-丙二硫醇 、 氢氟酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 29.0h， 生成 (8R)-3-cyclopentyl-8-hydroxy-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepine
  参考文献：
  名称：

  Enantiospecific Synthesis of Carbapentostatins

  摘要：

  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.

  DOI：

  10.1021/jo020612x
• 作为产物：
  描述：

  (2S,3R)-2-Amino-4-azido-3-<(tert-butyldimethylsilyl)oxy>butyronitrile 以 2,2,2-三氟乙醇 、 1,2-二氯乙烷 为溶剂， 反应 8.0h， 生成 5-[(R)-2-Azido-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-cyclopentyl-3H-imidazol-4-ylamine
  参考文献：
  名称：

  Enantiospecific Synthesis of Carbapentostatins

  摘要：

  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.

  DOI：

  10.1021/jo020612x