2,4,6-Trimethyl-benzenesulfonic acid 2-azido-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl ester | 404839-78-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2,4,6-Trimethyl-benzenesulfonic acid 2-azido-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl ester
• 英文别名: [2-azido-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl] 2,4,6-trimethylbenzenesulfonate
• CAS: 404839-78-7
• 化学式: C₁₉H₂₁N₇O₆S
• 分子量: 475.485
• InChiKey: JLGGMSMWLCGEGO-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  159
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,4,6-Trimethyl-benzenesulfonic acid 2-azido-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl ester 在 ammonium hydroxide 、 亚磷酸二苯酯 、 碘 、 双(2-氧代-3-恶唑烷基)次磷酰氯 作用下， 以 1,4-二氧六环 、 吡啶 、 水 为溶剂， 反应 67.0h， 生成 2-azido-2'-deoxyadenyl(5'-3')thymidine
  参考文献：
  名称：

  Synthesis and properties of 2-azidodeoxyadenosine and its incorporation into oligodeoxynucleotides

  摘要：

  2-Azidodeoxyadenosine (7) was conveniently synthesized from deoxyguanosine (2) by use of a combined reagent of TMSN3-BuONO. The Structure Of the tautomer of the azido derivative was determined by H-1 NMR. Reaction of 7 with iPr(2)NP(OEt)(2) gave an intermediate 10 of the Staudinger reaction. Incorporation of 7 into a DNA 13mer resulted in a significant decrease of the T-m value of the DNA duplex upon hybridization with the complementary strand. The thermal stability was discussed based on the hydrogen bond energy and electrostatic repulsion. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02028-7
• 作为产物：
  描述：

  2,4,6-Trimethyl-benzenesulfonic acid 2-amino-9-((2R,4S,5R)-4-trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl ester 在 亚硝酸丁酯 、 叠氮基三甲基硅烷 作用下， 以 二氯甲烷 、 甲醇 、 水 为溶剂， 反应 25.0h， 以45%的产率得到2,4,6-Trimethyl-benzenesulfonic acid 2-azido-9-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl ester
  参考文献：
  名称：

  Synthesis and properties of 2-azidodeoxyadenosine and its incorporation into oligodeoxynucleotides

  摘要：

  2-Azidodeoxyadenosine (7) was conveniently synthesized from deoxyguanosine (2) by use of a combined reagent of TMSN3-BuONO. The Structure Of the tautomer of the azido derivative was determined by H-1 NMR. Reaction of 7 with iPr(2)NP(OEt)(2) gave an intermediate 10 of the Staudinger reaction. Incorporation of 7 into a DNA 13mer resulted in a significant decrease of the T-m value of the DNA duplex upon hybridization with the complementary strand. The thermal stability was discussed based on the hydrogen bond energy and electrostatic repulsion. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02028-7