N²,O^5'-ditrityl-2-amino-6-chloro-9-[3-O-(tetrahydro-2-pyranyl)-β-D-arabinofuranosyl]purine | 1053641-60-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N²,O^5'-ditrityl-2-amino-6-chloro-9-[3-O-(tetrahydro-2-pyranyl)-β-D-arabinofuranosyl]purine
• 英文别名: (2R,3S,4S,5R)-2-[6-chloro-2-(tritylamino)purin-9-yl]-4-(oxan-2-yloxy)-5-(trityloxymethyl)oxolan-3-ol
• CAS: 1053641-60-3
• 化学式: C₅₃H₄₈ClN₅O₅
• 分子量: 870.448
• InChiKey: FMDLWQBNLUXJRD-XJUDLYIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  64
• 可旋转键数：
  14
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N²,O^5'-ditrityl-2-amino-6-chloro-9-[3-O-(tetrahydro-2-pyranyl)-β-D-arabinofuranosyl]purine 在 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 6.0h， 以60%的产率得到N²,O^5'-ditrityl-2-amino-6-chloro-9-[2-deoxy-2-fluoro-3-O-(tetrahydro-2-pyranyl)-β-D-ribofuranosyl]purine
  参考文献：
  名称：

  SYNTHESIS of 2′-DEOXY-2′-FLUOROGUANYL-(3′,5′)-GUANOSINE

  摘要：

  The protected analogue of 2-amnio-6-chloropurine arabinoside (3b) was subjected to reaction with diethylaminosulfur trifluoride (DAST) and subsequently treated with NaOAc in Ac2O/AcOH to give N-2, O-3', O-5'-triacetyl-2'-deoxy-2'-fluoroguanosine (5a). After deacetylation of the sugar moiety and protection of 5'-OH by a 4,4'-dimethoxytrityl group, this nucleoside component was converted to 2'-deoxy-2-fluoroguanyl-(3',5')-guanosine (6c, GfpG).

  DOI：

  10.1081/ncn-120016479
• 作为产物：
  描述：

  2-amino-6-chloro-9-[2-O-trifluoromethanesulfonyl-3,5-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanyl)-β-D-ribofuranosyl]purine 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 N²,O^5'-ditrityl-2-amino-6-chloro-9-[3-O-(tetrahydro-2-pyranyl)-β-D-arabinofuranosyl]purine
  参考文献：
  名称：

  SYNTHESIS of 2′-DEOXY-2′-FLUOROGUANYL-(3′,5′)-GUANOSINE

  摘要：

  The protected analogue of 2-amnio-6-chloropurine arabinoside (3b) was subjected to reaction with diethylaminosulfur trifluoride (DAST) and subsequently treated with NaOAc in Ac2O/AcOH to give N-2, O-3', O-5'-triacetyl-2'-deoxy-2'-fluoroguanosine (5a). After deacetylation of the sugar moiety and protection of 5'-OH by a 4,4'-dimethoxytrityl group, this nucleoside component was converted to 2'-deoxy-2-fluoroguanyl-(3',5')-guanosine (6c, GfpG).

  DOI：

  10.1081/ncn-120016479

文献信息

• SYNTHESIS of 2′-DEOXY-2′-FLUOROGUANYL-(3′,5′)-GUANOSINE
  作者：Tokumi Maruyama、Shigetada Kozai、Kazuo Nakamura、Masachika Irie

  DOI：10.1081/ncn-120016479

  日期：2002.12.31

  The protected analogue of 2-amnio-6-chloropurine arabinoside (3b) was subjected to reaction with diethylaminosulfur trifluoride (DAST) and subsequently treated with NaOAc in Ac2O/AcOH to give N-2, O-3', O-5'-triacetyl-2'-deoxy-2'-fluoroguanosine (5a). After deacetylation of the sugar moiety and protection of 5'-OH by a 4,4'-dimethoxytrityl group, this nucleoside component was converted to 2'-deoxy-2-fluoroguanyl-(3',5')-guanosine (6c, GfpG).