3'-(S)-(cytosin-1-yl)-4'-(R)-hydroxy-5'-(S)-hydroxymethyl-tetrahydrofuran | 178962-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3'-(S)-(cytosin-1-yl)-4'-(R)-hydroxy-5'-(S)-hydroxymethyl-tetrahydrofuran
• 英文别名: 2-(4-Amino-2-oxo-1(2H)-pyrimidinyl)-1,4-anhydro-2-deoxy-L-arabinitol；4-amino-1-[(3S,4R,5S)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]pyrimidin-2-one
• CAS: 178962-10-2
• 化学式: C₉H₁₃N₃O₄
• 分子量: 227.22
• InChiKey: YQZIOPLVSOBQKZ-VMHSAVOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3'-(S)-(cytosin-1-yl)-4'-(R)-hydroxy-5'-(S)-hydroxymethyl-tetrahydrofuran 在 吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 72.17h， 生成 [(2S,3R,4S)-4-(4-amino-2-oxopyrimidin-1-yl)-2-(hydroxymethyl)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：

  1-[(3S,4R,5R)-5-(dimethoxymethyl)-4-hydroxyoxolan-3-yl]pyrimidine-2,4-dione 在 吡啶 、 1H-1,2,3-三氮唑 、 ammonium hydroxide 、 sodium tetrahydroborate 、 三乙胺 、 三氟乙酸 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 22.17h， 生成 3'-(S)-(cytosin-1-yl)-4'-(R)-hydroxy-5'-(S)-hydroxymethyl-tetrahydrofuran
  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

• 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.