N-[9-((3aR,4R,6R,6aR)-2-Dimethylamino-6-hydroxymethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-2-phenoxy-acetamide | 226558-71-0

• 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: N-[9-((3aR,4R,6R,6aR)-2-Dimethylamino-6-hydroxymethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-2-phenoxy-acetamide
• CAS: 226558-71-0
• 化学式: C₂₁H₂₄N₆O₇
• 分子量: 472.458
• InChiKey: JCZBJTLHGGHPLB-POGBZWEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.34
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  153.06
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N-[9-((3aR,4R,6R,6aR)-2-Dimethylamino-6-hydroxymethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-2-phenoxy-acetamide 在 吡啶 、 potassium phosphate 、 磷酸单苯酯 、 金刚烷酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 甘油 作用下， 以 吡啶 为溶剂， 反应 50.17h， 生成 5′-O-(dimethoxytrityl)-2′-O-(tert-butyldimethylsilyl)-N2-phenoxyacetylguanosine
  参考文献：
  名称：

  High yield protection of purine ribonucleosides for phosphoramidite RNA synthesis

  摘要：

  We report high yield procedures for protection of purine ribonucleosides based on a reaction which allows concomitant highly regiospecific 2'-silylation and 3'-phosphitylation. Subsequent cleavage of the H-phosphonate monoester moiety without silyl migration provides intermediates ready for phosphitylation by standard methods to give fully protected phosphoramidites. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00733-9
• 作为产物：
  描述：

  phenoxyacetyl-1-O-benzotriazolide 在 吡啶 、 三甲基氯硅烷 作用下， 反应 38.0h， 生成 N-[9-((3aR,4R,6R,6aR)-2-Dimethylamino-6-hydroxymethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-2-phenoxy-acetamide
  参考文献：
  名称：

  High yield protection of purine ribonucleosides for phosphoramidite RNA synthesis

  摘要：

  We report high yield procedures for protection of purine ribonucleosides based on a reaction which allows concomitant highly regiospecific 2'-silylation and 3'-phosphitylation. Subsequent cleavage of the H-phosphonate monoester moiety without silyl migration provides intermediates ready for phosphitylation by standard methods to give fully protected phosphoramidites. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00733-9