1-benzimidazolyl-5-O-benzyl-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-β-D-ribofuranose | 403731-51-1

• 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: 1-benzimidazolyl-5-O-benzyl-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-β-D-ribofuranose
• 英文别名: (2R,3S,4S,5R,6R)-6-[(2R,3S,4R,5R)-5-(benzimidazol-1-yl)-4-hydroxy-2-(phenylmethoxymethyl)oxolan-3-yl]oxy-5-phenylmethoxy-2-(phenylmethoxymethyl)oxane-3,4-diol
• CAS: 403731-51-1
• 化学式: C₃₉H₄₂N₂O₉
• 分子量: 682.77
• InChiKey: ODNBAXIHTCTZDX-KXRYOXNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  50
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  二苯基N,N'-二异丙基亚磷酰胺 、 1-benzimidazolyl-5-O-benzyl-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-β-D-ribofuranose 在 四氮唑 作用下， 以 二氯甲烷 为溶剂， 生成 Phosphorous acid (2R,3R,4R,5R,6R)-6-[(2R,3R,4R,5R)-5-benzoimidazol-1-yl-2-benzyloxymethyl-4-(bis-benzyloxy-phosphanyloxy)-tetrahydro-furan-3-yloxy]-5-benzyloxy-2-benzyloxymethyl-4-(bis-benzyloxy-phosphanyloxy)-tetrahydro-pyran-3-yl ester dibenzyl ester
  参考文献：
  名称：

  通过碱基置换策略聚合合成腺苷 A 类似物

  摘要：

  天然产物的第一个完全合成的碱基修饰类似物和有效的 D-肌醇 1,4,5-三磷酸受体激动剂腺苷 A 是由 D-木糖和 D-葡萄糖使用碱基和替代碱基添加的方法有效合成的一种常见的二糖中间体。

  DOI：

  10.1039/a909347h
• 作为产物：
  描述：

  allyl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside 在 吡啶 、 四氮唑 、 三甲基氯硅烷 、 4 A molecular sieve 、 氨 、 水 、 silver perchlorate 、 溶剂黄146 、 六甲基二硅氮烷 、 palladium dichloride 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 乙二醇 、 甲苯 为溶剂， 反应 65.75h， 生成 1-benzimidazolyl-5-O-benzyl-3-O-(2,6-di-O-benzyl-α-D-glucopyranosyl)-β-D-ribofuranose
  参考文献：
  名称：

  通过碱基置换策略聚合合成腺苷 A 类似物

  摘要：

  天然产物的第一个完全合成的碱基修饰类似物和有效的 D-肌醇 1,4,5-三磷酸受体激动剂腺苷 A 是由 D-木糖和 D-葡萄糖使用碱基和替代碱基添加的方法有效合成的一种常见的二糖中间体。

  DOI：

  10.1039/a909347h

文献信息

• Total Synthesis of Nucleobase-Modified Adenophostin A Mimics
  作者：Satoshi Shuto、Graeme Horne、Rachel D. Marwood、Barry V. L. Potter

  DOI：10.1002/1521-3765(20011119)7:22<4937::aid-chem4937>3.0.co;2-g

  日期：2001.11.19

  The adenophostins exhibit approximately 10-100 times higher receptor binding and Ca2+ mobilising potencies in comparison with the natural second messenger D-myo-inositol 1,4,5-trisphosphate [Ins(1,4,5)P-3]. Despite many synthetic attempts to determine the minimal structural requirement for this unusual behaviour of the adenophostins, few related simplified analogues displaying higher activity than that of Ins(1.4,5)P-3 have been reported. However, biological evaluation of such analogues has revealed that one of the key factors for the enhanced biological activity is the adenine moiety. To further understand the effect that the adenine base has upon the activity of the adenophostins, congeners in which this functionality is replaced by uracil, benzimidazole, 2-methoxynaphthalene, 4-methylanisole and 4-methylnaphthalene using the common intermediate 1,2-di-O-acetyl-5-O-benzyl-3-O-(3,4-di-O-acetyl-2,6-di-O-benzyl-alpha -D-glucopyranosyl)-ribofuranose have been synthesised using a base replacement strategy. The synthesis of the uracil and benzimidazole analogues was achieved using the Vorbruggen condensation procedure. The 1'-C-glycosidic analogues were prepared using Friedel-Crafts type C-aryl glycosidation reactions. Phosphate groups were introduced using the phosphoramidite method with subsequent removal of all-benzyl protecting groups by catalytic hydrogenation or catalytic hydrogen transfer. Apart from one analogue with an alpha -glycosidic linkage all compounds were more potent than Ins(1,4,5)P-3 and most tended more towards adenophostin in activity. These analogues will be valuable tools to unravel the role that the adenine moiety plays in the potent activity of the adenophostins and demonstrate that this strategy is effective at producing highly potent ligands.