N-{9-[(2R,3R,4R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzyloxy)-4-methylsulfanylmethoxy-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide | 190968-28-6

• 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-[(2R,3R,4R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzyloxy)-4-methylsulfanylmethoxy-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide
• CAS: 190968-28-6
• 化学式: C₄₃H₄₇N₅O₆SSi
• 分子量: 790.028
• InChiKey: WRNTYCZTQCFAHE-GNECSJIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.85
• 重原子数：
  56.0
• 可旋转键数：
  15.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  118.85
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  磷酸二丁酯 、 N-{9-[(2R,3R,4R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzyloxy)-4-methylsulfanylmethoxy-tetrahydro-furan-2-yl]-9H-purin-6-yl}-benzamide 在 N-碘代丁二酰亚胺 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以72%的产率得到Phosphoric acid (2R,3R,4R,5R)-5-(6-benzoylamino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-3-yloxymethyl ester dibutyl ester
  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：

  2'-O-(4-methoxybenzyl)-N⁶-benzoyladenosine 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 过氧化氢苯甲酰 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 2.5h， 生成 N-{9-[(2R,3R,4R,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzyloxy)-4-methylsulfanylmethoxy-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