N-[9-(2-{(2S,3R,4S,5S,6R)-3-Benzyloxy-6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4,5-dihydroxy-tetrahydro-pyran-2-yloxy}-ethoxymethyl)-9H-purin-6-yl]-benzamide | 190779-81-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-[9-(2-{(2S,3R,4S,5S,6R)-3-Benzyloxy-6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4,5-dihydroxy-tetrahydro-pyran-2-yloxy}-ethoxymethyl)-9H-purin-6-yl]-benzamide
• CAS: 190779-81-8
• 化学式: C₄₉H₄₉N₅O₁₀
• 分子量: 867.956
• InChiKey: UJBPJJZOYMESFH-ORSDTHNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.13
• 重原子数：
  64.0
• 可旋转键数：
  19.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  177.77
• 氢给体数：
  3.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  N-[9-(2-{(2S,3R,4S,5S,6R)-3-Benzyloxy-6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4,5-dihydroxy-tetrahydro-pyran-2-yloxy}-ethoxymethyl)-9H-purin-6-yl]-benzamide 在 四氮唑 、 叔丁基过氧化氢 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.33h， 生成 Phosphoric acid (2S,3R,4R,5R,6R)-2-[2-(6-benzoylamino-purin-9-ylmethoxy)-ethoxy]-3-benzyloxy-5-[bis-(2-methanesulfonyl-ethoxy)-phosphoryloxy]-6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-pyran-4-yl ester bis-(2-methanesulfonyl-ethyl) ester
  参考文献：
  名称：

  Synthesis of 3″,4″-bisphosphate-containing analogs of adenophostin A

  摘要：

  Glycosylation of ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-alpha/beta-D-glucopyranoside (6) with tert-butyldiphenylsilylglycol (7) or 1,2-di-O-p-methoxybenzyl-sn-glycerol (16) under the agency of N-iodosuccinimide/triflic acid afforded alpha-glucosides 8 and 17, respectively. Protective group manipulations (8 --> 10 and 17 --> 20) and acetolysis of the methylthiomethyl functions yielded 2-O-(3,4,6-tri-O-acetyl-2-O-benzyl-alpha-D-glucopyranosyl)-1-O-acetoxymethylglycol (11) and 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-alpha-D-glucopyranosyl)-2-O-acetoxymethyl-1-O-tert-butyldiphenylsilyl-sn-glycerol (21). Vorbruggen condensation with silylated 6-N-benzoyladenine (22), subsequent protective group manipulations on 23 and 29 followed by phosphorylation furnished, after purification, homogeneous glycol-based adenophostin A analog 4 and glycerol-based analog 5. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00309-8
• 作为产物：
  描述：

  N6-苯甲酰基腺嘌呤 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 potassium tert-butylate 作用下， 以 1,4-二氧六环 、 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 25.02h， 生成 N-[9-(2-{(2S,3R,4S,5S,6R)-3-Benzyloxy-6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4,5-dihydroxy-tetrahydro-pyran-2-yloxy}-ethoxymethyl)-9H-purin-6-yl]-benzamide
  参考文献：
  名称：

  Synthesis of 3″,4″-bisphosphate-containing analogs of adenophostin A

  摘要：

  Glycosylation of ethyl 3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-alpha/beta-D-glucopyranoside (6) with tert-butyldiphenylsilylglycol (7) or 1,2-di-O-p-methoxybenzyl-sn-glycerol (16) under the agency of N-iodosuccinimide/triflic acid afforded alpha-glucosides 8 and 17, respectively. Protective group manipulations (8 --> 10 and 17 --> 20) and acetolysis of the methylthiomethyl functions yielded 2-O-(3,4,6-tri-O-acetyl-2-O-benzyl-alpha-D-glucopyranosyl)-1-O-acetoxymethylglycol (11) and 3-O-(3,4,6-tri-O-acetyl-2-O-benzyl-alpha-D-glucopyranosyl)-2-O-acetoxymethyl-1-O-tert-butyldiphenylsilyl-sn-glycerol (21). Vorbruggen condensation with silylated 6-N-benzoyladenine (22), subsequent protective group manipulations on 23 and 29 followed by phosphorylation furnished, after purification, homogeneous glycol-based adenophostin A analog 4 and glycerol-based analog 5. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00309-8