O⁶-Benzyl-N²,3-etheno-2'-O--3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl)guanosine | 148437-93-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O⁶-Benzyl-N²,3-etheno-2'-O--3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl)guanosine
• 英文别名: O⁶-Benzyl-N²,3-etheno-2'-O-[phenoxy(thiocarbonyl)]-3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl)guanosine；[(6aR,8R,9R,9aR)-8-(4-phenylmethoxyimidazo[2,1-b]purin-1-yl)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl]oxy-phenoxymethanethione
• CAS: 148437-93-8
• 化学式: C₃₈H₄₉N₅O₇SSi₂
• 分子量: 776.073
• InChiKey: QUXFYGIIXJYECI-QGGAYTEESA-N

物化性质

• 溶解度：
  可溶于氯仿、DMSO、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  8.26
• 重原子数：
  53
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  O⁶-Benzyl-N²,3-etheno-2'-O--3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl)guanosine 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以65%的产率得到O6-苄基-N2,3-乙烯桥-2’-脱氧-3’,5’-O-[四(异丙基)-1,3-二硅氧烷二基]鸟苷
  参考文献：
  名称：

  N2,3-etheno-2'-deoxyguanosine [8,9-dihydro-9-oxo-2'-deoxy-3-.beta.-D-ribofuranosylimidazo[2,1-b]purine]: a practical synthesis and characterization

  摘要：

  The literature methods for the syntheses of N2,3-etheno-2'-deoxyguanosine (1a) and its 5'-O-phosphate are associated with very low overall yields. We now describe a route starting in the riboside series that permits the production of 1a in practical quantities and has allowed its complete chemical characterization for the first time. O6-Benzylguanosine (6b) when treated with bromoacetaldehyde under conditions of continuous buffering gives the N2,3-etheno derivative 7b in 48% yield. The 3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl) derivative (8b, 89 % yield) of 7b when allowed to react with phenyl chlorothionoformate led to the corresponding 2' ester (10,50%). 2'-Deoxygenation of 10 by the Barton procedure then afforded 65% of 11, and deprotection of the latter (Bu4N+F-) gave 12 quantitatively. Catalytic hydrogenation of 12 then produced pure la in 86% yield. Stability studies on la have confirmed its exquisite sensitivity to acid and demonstrated its relative stability to alkali and the other reagents used in automated DNA synthesis (phosphoramidate method).

  DOI：

  10.1021/jo00061a033
• 作为产物：
  描述：

  O6-苄基鸟苷 在 吡啶 、 4-二甲氨基吡啶 、 sodium acetate 、 溶剂黄146 、 potassium iodide 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 54.0h， 生成 O⁶-Benzyl-N²,3-etheno-2'-O--3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl)guanosine
  参考文献：
  名称：

  N2,3-etheno-2'-deoxyguanosine [8,9-dihydro-9-oxo-2'-deoxy-3-.beta.-D-ribofuranosylimidazo[2,1-b]purine]: a practical synthesis and characterization

  摘要：

  The literature methods for the syntheses of N2,3-etheno-2'-deoxyguanosine (1a) and its 5'-O-phosphate are associated with very low overall yields. We now describe a route starting in the riboside series that permits the production of 1a in practical quantities and has allowed its complete chemical characterization for the first time. O6-Benzylguanosine (6b) when treated with bromoacetaldehyde under conditions of continuous buffering gives the N2,3-etheno derivative 7b in 48% yield. The 3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl) derivative (8b, 89 % yield) of 7b when allowed to react with phenyl chlorothionoformate led to the corresponding 2' ester (10,50%). 2'-Deoxygenation of 10 by the Barton procedure then afforded 65% of 11, and deprotection of the latter (Bu4N+F-) gave 12 quantitatively. Catalytic hydrogenation of 12 then produced pure la in 86% yield. Stability studies on la have confirmed its exquisite sensitivity to acid and demonstrated its relative stability to alkali and the other reagents used in automated DNA synthesis (phosphoramidate method).

  DOI：

  10.1021/jo00061a033

文献信息

• N2,3-etheno-2'-deoxyguanosine [8,9-dihydro-9-oxo-2'-deoxy-3-.beta.-D-ribofuranosylimidazo[2,1-b]purine]: a practical synthesis and characterization
  作者：Rajesh Khazanchi、Pei Lin Yu、Francis Johnson

  DOI：10.1021/jo00061a033

  日期：1993.4

  The literature methods for the syntheses of N2,3-etheno-2'-deoxyguanosine (1a) and its 5'-O-phosphate are associated with very low overall yields. We now describe a route starting in the riboside series that permits the production of 1a in practical quantities and has allowed its complete chemical characterization for the first time. O6-Benzylguanosine (6b) when treated with bromoacetaldehyde under conditions of continuous buffering gives the N2,3-etheno derivative 7b in 48% yield. The 3',5'-O-(1,1,3,3-tetraisopropyldisiloxa-1,3-diyl) derivative (8b, 89 % yield) of 7b when allowed to react with phenyl chlorothionoformate led to the corresponding 2' ester (10,50%). 2'-Deoxygenation of 10 by the Barton procedure then afforded 65% of 11, and deprotection of the latter (Bu4N+F-) gave 12 quantitatively. Catalytic hydrogenation of 12 then produced pure la in 86% yield. Stability studies on la have confirmed its exquisite sensitivity to acid and demonstrated its relative stability to alkali and the other reagents used in automated DNA synthesis (phosphoramidate method).