2-(6-Amino-9H-purin-9-YL)-1,4-anhydro-2-deoxy-L-arabinitol | 174955-57-8

• 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: 2-(6-Amino-9H-purin-9-YL)-1,4-anhydro-2-deoxy-L-arabinitol
• 英文别名: (2S,3R,4S)-4-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 174955-57-8
• 化学式: C₁₀H₁₃N₅O₃
• 分子量: 251.245
• InChiKey: XLAFLMYNXDUGLH-VMHSAVOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  18
• 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：
  119
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(6-Amino-9H-purin-9-YL)-1,4-anhydro-2-deoxy-L-arabinitol 在 吡啶 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 72.34h， 生成 [(2S,3R,4S)-4-(6-acetamidopurin-9-yl)-2-[(4-oxo-1,3,2-benzodioxaphosphinin-2-yl)oxymethyl]oxolan-3-yl] acetate
  参考文献：
  名称：

  Synthesis of Isonucleoside 5′-Triphosphates

  摘要：

  A series of isonucleoside 5'-triphosphates were synthesized via a rapid and efficient method. The structures of the triphosphates (8a-8d) were characterized by (PNMR)-P-31 and TOF-MS.

  DOI：

  10.1081/scc-120020202
• 作为产物：
  描述：

  (2R,3R,4S)-4-(6-aminopurin-9-yl)-2-(dimethoxymethyl)oxolan-3-ol 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 反应 3.67h， 生成 2-(6-Amino-9H-purin-9-YL)-1,4-anhydro-2-deoxy-L-arabinitol
  参考文献：
  名称：

  Studies on the synthesis and biological activities of 4′-(R)-hydroxy-5′-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines

  摘要：

  A series of 4'-(R)-hydroxy-5'-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines were synthesized by the reaction of 3,4-epoxy-5-(S,trans)-dimethoxymethyl-tetrahydrofuran and nucleobases under the catalysis of potassium tert-butoxide and 18-crown-6. Compounds 6a, 6c and 7b have shown significant inhibition on the growth of HL-60 cells. The phosphotriester and phosphodiester of isonucleoside 8a-d were synthesized and cytotoxic activities were reported. The conformation of isonucleosides in solution was studied by H-1 NMR. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00048-x

文献信息

• Stereoselective synthesis of l-isonucleosides
  作者：Sı́lvia Aragonès、Fernando Bravo、Yolanda Dı́az、Ma̱ Isabel Matheu、Sergio Castillón

  DOI：10.1016/s0040-4039(03)00743-3

  日期：2003.5

  L-Isonucleosides 17 and 19 were stereoselectively synthesised from (S)-glycidol by two different procedures. The key step was the synthesis of a chiral dihydrofuran which was carried out by oxidation/elimination of 8 and by ring-closing metathesis of diene 10. The procedure can be applied to the synthesis of both enantiomers. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Studies on the synthesis and biological activities of 4′-(R)-hydroxy-5′-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines
  作者：Hong-Wu Yu、Liang-Ren Zhang、Ji-Chang Zhou、Ling-Tai Ma、Li-He Zhang

  DOI：10.1016/0968-0896(96)00048-x

  日期：1996.4

  A series of 4'-(R)-hydroxy-5'-(S)-hydroxymethyl-tetrahydrofuranyl purines and pyrimidines were synthesized by the reaction of 3,4-epoxy-5-(S,trans)-dimethoxymethyl-tetrahydrofuran and nucleobases under the catalysis of potassium tert-butoxide and 18-crown-6. Compounds 6a, 6c and 7b have shown significant inhibition on the growth of HL-60 cells. The phosphotriester and phosphodiester of isonucleoside 8a-d were synthesized and cytotoxic activities were reported. The conformation of isonucleosides in solution was studied by H-1 NMR. Copyright (C) 1996 Elsevier Science Ltd
• Synthesis of Isonucleoside 5′-Triphosphates
  作者：Kuiying Xu、Jimei Min、Lihe Zhang

  DOI：10.1081/scc-120020202

  日期：2003.6

  A series of isonucleoside 5'-triphosphates were synthesized via a rapid and efficient method. The structures of the triphosphates (8a-8d) were characterized by (PNMR)-P-31 and TOF-MS.