(2R,4R)-4-(6'-amino-9'H-purin-9'-yl)tetrahydrothiophene-2-methanol | 142952-69-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (2R,4R)-4-(6'-amino-9'H-purin-9'-yl)tetrahydrothiophene-2-methanol
• 英文别名: 6-amino-9-[(3R,5R)-5-(hydroxymethyl)tetrahydrothiophen-3-yl]purine；L-threo-Pentitol, 2-(6-amino-9H-purin-9-yl)-1,2,3,4-tetradeoxy-1,4-epithio-；[(2R,4R)-4-(6-aminopurin-9-yl)thiolan-2-yl]methanol
• CAS: 142952-69-0
• 化学式: C₁₀H₁₃N₅OS
• 分子量: 251.312
• InChiKey: JMKUQWUCPRVDDR-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,4-戊二烯 在 potassium osmate(VI) 、 氢化奎宁 1,4-(2,3-二氮杂萘)二醚 吡啶 、 4-二甲氨基吡啶 、 sodium sulfide 、 18-冠醚-6 、 四丁基氟化铵 、 sodium hydride 、 potassium carbonate 、 三乙胺 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 65.5h， 生成 (2R,4R)-4-(6'-amino-9'H-purin-9'-yl)tetrahydrothiophene-2-methanol
  参考文献：
  名称：

  Enantiospecific Total Synthesis of l-2‘,3‘-Dideoxyisonucleosides via Regioselective Opening of Optically Active C₂-Symmetric 1,4-Pentadiene Bis-epoxide¹

  摘要：

  A new method for the synthesis of L-2',3'-dideoxyisonucleosides is described. The readily available, optically active C-2-symmetric bis-epoxide (2S,4S)-1,2:4,5-diepoxypentane (5) was prepared by a short route from readily available starting materials. The key step of the new synthesis is the opening of 5 with nucleophiles, which proceeds highly regioselectively; e.g., reaction with sodium sulfide affords a 5:1 mixture of the tetrahydrothiophenediol 9a and the tetrahydrothiopyrandiol 14, and reaction with sodium hydroxide gives exclusively the tetrahydrofurandiol 9b via a preferred 5-exo cyclization. These five-membered diols 9a,b can be converted in only four steps into the modified dideoxyuridine and adenosine isonucleosides 4a-c, one of which (4c) has shown good antiviral activity. In addition, we have examined the opening of the analogous six carbon bis-epoxide, (2S,5S)-1,2:5,6-diepoxyhexane (23), which affords a 3:1 mixture of the hexahydrothiepinediol 24 and the tetrahydrothiopyrandiol 25 with sodium sulfide via a preferred 7-endo cyclization. An alternate route to these two optically active bis-epoxides 5 and 23 was also examined, namely the asymmetric dihydroxylation of 1,4-pentadiene and 1,5-hexadiene followed by selective sulfonylation and epoxide : formation. The asymmetric reaction produces a nearly 1:1 mixture of optically active and meso tetrols, e.g., 28-9 and 32-3. Unfortunately, the tetrols, their simple derivatives, and the final sulfonates and epoxides could not be readily separated by Rnv simple means.

  DOI：

  10.1021/jo9721655

文献信息

• Tetrahydrothiophene nucleosides as potential anti-HIV agents
  作者：Martin F. Jones、Stewart A. Noble、Colin A. Robertson、Richard Storer

  DOI：10.1016/0040-4039(91)80867-6

  日期：1991.1

  A series of novel tetrahydrothiophene nucleosides have been prepared in homochiral form from D-glucose and assessed as anti-HIV agents in whole cell assay.

  已经从D-葡萄糖以同手性形式制备了一系列新的四氢噻吩核苷，并在全细胞测定中被评估为抗HIV药物。
• Synthesis and Testing of New Modified Nucleosides
  作者：Michael E. Jung、Christopher J. Nichols、Oliver Kretschik、Yue Xu

  DOI：10.1080/15257779908041490

  日期：1999.4

  New efficient routes for the high-yielding synthesis of several classes of modified nucleosides have been developed. We have prepared both the D- and L-enantiomers of the methylene-expanded oxetanocin isonucleosides 1a-e and the L-2',3'-dideoxy isonucleosides 2abc (both the oxa and thia analgoues) as well as new routes for the preparation of L-ribose and 2-deoxy L-ribose 3ab and their modified nucleosides 4.
• Jones, Martin F.; Noble, Stewart A.; Robertson, Colin A., Journal of the Chemical Society. Perkin transactions I, 1992, # 11, p. 1427 - 1436
  作者：Jones, Martin F.、Noble, Stewart A.、Robertson, Colin A.、Storer, Richard、Highcock, Rona M.、Lamont, R. Brian

  DOI：——

  日期：——
• Enantiospecific Total Synthesis of <scp>l</scp>-2‘,3‘-Dideoxyisonucleosides via Regioselective Opening of Optically Active <i>C</i>₂-Symmetric 1,4-Pentadiene Bis-epoxide¹
  作者：Michael E. Jung、Oliver Kretschik

  DOI：10.1021/jo9721655

  日期：1998.5.1

  A new method for the synthesis of L-2',3'-dideoxyisonucleosides is described. The readily available, optically active C-2-symmetric bis-epoxide (2S,4S)-1,2:4,5-diepoxypentane (5) was prepared by a short route from readily available starting materials. The key step of the new synthesis is the opening of 5 with nucleophiles, which proceeds highly regioselectively; e.g., reaction with sodium sulfide affords a 5:1 mixture of the tetrahydrothiophenediol 9a and the tetrahydrothiopyrandiol 14, and reaction with sodium hydroxide gives exclusively the tetrahydrofurandiol 9b via a preferred 5-exo cyclization. These five-membered diols 9a,b can be converted in only four steps into the modified dideoxyuridine and adenosine isonucleosides 4a-c, one of which (4c) has shown good antiviral activity. In addition, we have examined the opening of the analogous six carbon bis-epoxide, (2S,5S)-1,2:5,6-diepoxyhexane (23), which affords a 3:1 mixture of the hexahydrothiepinediol 24 and the tetrahydrothiopyrandiol 25 with sodium sulfide via a preferred 7-endo cyclization. An alternate route to these two optically active bis-epoxides 5 and 23 was also examined, namely the asymmetric dihydroxylation of 1,4-pentadiene and 1,5-hexadiene followed by selective sulfonylation and epoxide : formation. The asymmetric reaction produces a nearly 1:1 mixture of optically active and meso tetrols, e.g., 28-9 and 32-3. Unfortunately, the tetrols, their simple derivatives, and the final sulfonates and epoxides could not be readily separated by Rnv simple means.