(8R)-3-[(1S,2R,4R)-2-(benzoyloxymethyl)-1-benzoyloxycyclopent-4-yl]-8-[(tert-butyldimethylsilyl)oxy]-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepine | 493039-15-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑二氮卓类
• 英文名称: (8R)-3-[(1S,2R,4R)-2-(benzoyloxymethyl)-1-benzoyloxycyclopent-4-yl]-8-[(tert-butyldimethylsilyl)oxy]-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepine
• 英文别名: [(1R,2S,4R)-2-benzoyloxy-4-[(8R)-8-[tert-butyl(dimethyl)silyl]oxy-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-3-yl]cyclopentyl]methyl benzoate
• CAS: 493039-15-9
• 化学式: C₃₂H₄₀N₄O₅Si
• 分子量: 588.779
• InChiKey: RDZMTPFTWGLGHF-JVYGEBFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.43
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (8R)-3-[(1S,2R,4R)-2-(benzoyloxymethyl)-1-benzoyloxycyclopent-4-yl]-8-[(tert-butyldimethylsilyl)oxy]-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepine 在 氢氟酸 、 lithium hydroxide 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 甲醇 为溶剂， 以55%的产率得到(8R)-3-[(1R,3S,4R)-(3-hydroxy-4-hydroxymethyl)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：

  (1S,2R,4R)-4-amino-1-benzoyloxy-2-(benzoyloxymethyl)cyclopentane 在 1,3-丙二硫醇 、 三乙胺 作用下， 以 甲醇 、 2,2,2-三氟乙醇 、 1,2-二氯乙烷 为溶剂， 反应 17.0h， 生成 (8R)-3-[(1S,2R,4R)-2-(benzoyloxymethyl)-1-benzoyloxycyclopent-4-yl]-8-[(tert-butyldimethylsilyl)oxy]-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

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.