N-{9-[(2R,3R,4R,5R)-4-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-4-hydroxy-butoxymethoxy)-5-hydroxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide | 190968-31-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-{9-[(2R,3R,4R,5R)-4-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-4-hydroxy-butoxymethoxy)-5-hydroxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide
• CAS: 190968-31-1
• 化学式: C₅₂H₅₅N₅O₁₁
• 分子量: 926.036
• InChiKey: IZLPZIYDAKGYTG-RTBBCTCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.67
• 重原子数：
  68.0
• 可旋转键数：
  25.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  187.0
• 氢给体数：
  3.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  N-{9-[(2R,3R,4R,5R)-4-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-4-hydroxy-butoxymethoxy)-5-hydroxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide 在 钯 4-二甲氨基吡啶 、 氢气 作用下， 以 吡啶 、 水 、 叔丁醇 为溶剂， 反应 50.0h， 生成
  参考文献：
  名称：

  Synthesis of 2′,3″,4″-trisphosphate-containing analogs of adenophostin A

  摘要：

  Adenophostin A analog 4 was prepared via trimethylsilyl trifluoromethanesulfonate (TMSOTf)-assisted glycosylation of (S)-6-N-diphenylacetyl-9-(2-tert-butyldiphenylsilyloxy-1-hydroxyprop-3-yl)-adenine (11) with trichloroacetimidate donor 12 to give dimer 13. Protective group manipulations on 13 followed by phosphitylation with N,N-diisopropyl-bis-[2-(methylsulfonyl)ethyl] phosphoramidite (17) and in situ oxidation gave, after deprotection, (25)-9-{1-(alpha-D-glucopyranosyloxy 3,4-bisphosphate)-2-monophosphate-prop-3-yl}-adenine (4) Condensation of phosphoryloxymethyladenosine 25 with D-arabinitol derivative 21 under the agency of TMSOTf afforded methylene acetal 26. Protective group manipulations (--> 32), phosphorylation, and deprotection yielded 3'-O-(D-arabinitol-4-O-methylene 2,3-bisphosphate)-adenosine 2'-monophosphate (5), a methylene acetal-containing analog of adenophostin A. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00308-6
• 作为产物：
  描述：

  N-{9-[(2R,3R,4R,5R)-4-[(1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-4-(tert-butyl-diphenyl-silanyloxy)-butoxymethoxy]-5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide 在 四丁基氟化铵 、 吡啶盐酸盐 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以75%的产率得到N-{9-[(2R,3R,4R,5R)-4-((1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-4-hydroxy-butoxymethoxy)-5-hydroxymethyl-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide
  参考文献：
  名称：

  Synthesis of 2′,3″,4″-trisphosphate-containing analogs of adenophostin A

  摘要：

  Adenophostin A analog 4 was prepared via trimethylsilyl trifluoromethanesulfonate (TMSOTf)-assisted glycosylation of (S)-6-N-diphenylacetyl-9-(2-tert-butyldiphenylsilyloxy-1-hydroxyprop-3-yl)-adenine (11) with trichloroacetimidate donor 12 to give dimer 13. Protective group manipulations on 13 followed by phosphitylation with N,N-diisopropyl-bis-[2-(methylsulfonyl)ethyl] phosphoramidite (17) and in situ oxidation gave, after deprotection, (25)-9-{1-(alpha-D-glucopyranosyloxy 3,4-bisphosphate)-2-monophosphate-prop-3-yl}-adenine (4) Condensation of phosphoryloxymethyladenosine 25 with D-arabinitol derivative 21 under the agency of TMSOTf afforded methylene acetal 26. Protective group manipulations (--> 32), phosphorylation, and deprotection yielded 3'-O-(D-arabinitol-4-O-methylene 2,3-bisphosphate)-adenosine 2'-monophosphate (5), a methylene acetal-containing analog of adenophostin A. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00308-6