(1S,2R,3S,5S)-2-<3-(6-chloro-5-nitropyrimidin-4-ylamino)bicyclo<3.1.0>hex-2-yl>ethanol | 219707-85-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (1S,2R,3S,5S)-2-<3-(6-chloro-5-nitropyrimidin-4-ylamino)bicyclo<3.1.0>hex-2-yl>ethanol
• 英文别名: 2-[(1S,2S,3S,5S)-3-[(6-chloro-5-nitropyrimidin-4-yl)amino]-2-bicyclo[3.1.0]hexanyl]ethanol
• CAS: 219707-85-4
• 化学式: C₁₂H₁₅ClN₄O₃
• 分子量: 298.729
• InChiKey: KCVVVFAXYZLFIT-JBDRJPRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,5S)-2-<3-(6-chloro-5-nitropyrimidin-4-ylamino)bicyclo<3.1.0>hex-2-yl>ethanol 在 盐酸 、 氨 、 tin(ll) chloride 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 17.5h， 生成 (1S,2R,3S,5S)-2-<3-(6-aminopurin-9-yl)bicyclo<3.1.0>hex-2-yl>ethanol
  参考文献：
  名称：

  Enantiomeric synthesis of nucleosides

  摘要：

  The total synthesis of L- (or 1S,2R,3S,5S)-bicarbocyclic nucleosides (8-15) has been accomplished. The key intermediate 3 was synthesized in two steps from the known chiral compound 1 through a stereoselective cyclopropanation under Furukawa conditions and its X-ray structure has been determined. The derivative 4 was utilized to obtain thymine derivative (8). Amine exocyclic pyrimidine (9-12) and purine (13-15) bicarbocyclic L-nucleosides were obtained from the (IS,2R,3S,5S)-2-(3-aminobicyclo[3.1.0]hex-2-yl)ethanol (7). (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00424-x
• 作为产物：
  描述：

  (1S,2R,3R,5S)-2-(3-hydroxybicyclo<3.1.0>hex-2-yl)ethanol tert-butyldimethylsilane ether 在 palladium on activated charcoal 吡啶 、 sodium azide 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (1S,2R,3S,5S)-2-<3-(6-chloro-5-nitropyrimidin-4-ylamino)bicyclo<3.1.0>hex-2-yl>ethanol
  参考文献：
  名称：

  立体选择性合成α-1-二碳环核苷作为潜在的抗病毒药物

  摘要：

  描述了迄今未知的碳环α-L-异构双环[3.1.0]己基核苷（8-11）的合成。在古河条件下，通过立体选择性环丙烷化，由已知的手性化合物1分七个步骤合成了关键中间体7。在HepG2T14细胞中，化合物8-11被评估为抗HBV药物。

  DOI：

  10.1016/s0040-4039(98)02137-6

文献信息

• Stereoselective synthesis of α-l-bicarbocyclic nucleosides as potential antiviral drugs
  作者：Christine Demaison、Christophe Hourioux、Philippe Roingeard、Luigi A. Agrofoglio

  DOI：10.1016/s0040-4039(98)02137-6

  日期：1998.12

  Synthesis of hitherto unknown carbocyclic α-L-isomeric bicyclo[3.1.0]hexyl nucleosides (8–11) is described. The key intermediate 7 was synthesized in seven steps from the known chiral compound 1 through a stereoselective cyclopropanation under Furukawa conditions. Compounds 8–11 were evaluated as anti-HBV agents in HepG2T14 cells.

  描述了迄今未知的碳环α-L-异构双环[3.1.0]己基核苷（8-11）的合成。在古河条件下，通过立体选择性环丙烷化，由已知的手性化合物1分七个步骤合成了关键中间体7。在HepG2T14细胞中，化合物8-11被评估为抗HBV药物。
• Stereoselective Synthesis of Carbocyclic α-L-Homonucleosides
  作者：L. A. Agrofoglio、F. Girard、C. Demaison、M-G. Lee、P. Roingeard、A. Fridland

  DOI：10.1080/15257779908041509

  日期：1999.4

  The synthesis of several optically pure carbocyclic alpha-1-isomeric homonucleosides [3a-e, 6a,b, 7a,b, 10a-d] is reported. The(1R, 5S)-2-oxabicyclo[3.3.0] oct-6-en-3-one 1 was used as a chiral starting material.
• Enantiomeric synthesis of nucleosides
  作者：Luigi A. Agrofoglio、Christine Demaison、Loïc Toupet

  DOI：10.1016/s0040-4020(99)00424-x

  日期：1999.6

  The total synthesis of L- (or 1S,2R,3S,5S)-bicarbocyclic nucleosides (8-15) has been accomplished. The key intermediate 3 was synthesized in two steps from the known chiral compound 1 through a stereoselective cyclopropanation under Furukawa conditions and its X-ray structure has been determined. The derivative 4 was utilized to obtain thymine derivative (8). Amine exocyclic pyrimidine (9-12) and purine (13-15) bicarbocyclic L-nucleosides were obtained from the (IS,2R,3S,5S)-2-(3-aminobicyclo[3.1.0]hex-2-yl)ethanol (7). (C) 1999 Elsevier Science Ltd. All rights reserved.