3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranoside | 264230-05-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranoside
• 英文别名: 3',4'-di-O-acetyl-2',5,6'-tri-O-benzyl-3-O-α-D-glucopyranosyl-1,2-O-isopropylidene-α-D-ribofuranose；[(2R,3R,4S,5R,6R)-6-[[(3aR,5R,6R,6aR)-2,2-dimethyl-5-(phenylmethoxymethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxy]-4-acetyloxy-5-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 264230-05-9
• 化学式: C₃₉H₄₆O₁₂
• 分子量: 706.787
• InChiKey: HTLGPXQGVKXBJD-IYCAMXROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  51
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranoside 在 4 A molecular sieve 、 四氯化锡 、 溶剂黄146 作用下， 以 吡啶 、 水 、 乙二醇 、 1,2-二氯乙烷 为溶剂， 反应 21.0h， 生成 1-((3-benzyloxycarbonylamino)-propyl)-2-O-acetyl-5-O-benzyl-3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-β-D-ribofuranoside
  参考文献：
  名称：

  Synthesis of Photoaffinity Derivatives of Adenophostin A

  摘要：

  DOI：

  10.1002/1099-0690(200009)2000:17<3085::aid-ejoc3085>3.0.co;2-a
• 作为产物：
  描述：

  5-O-benzyl-3-oxo-1,2-O-isopropylidene-α-D-xylofuranose 在 sodium tetrahydroborate 、 4 A molecular sieve 、 silver perchlorate 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 甲苯 为溶剂， 反应 21.0h， 生成 3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranoside
  参考文献：
  名称：

  使用碱基置换策略研究腺嘌呤碱基对腺苷A活性的贡献。

  摘要：

  3'-O-α-D-吡喃葡萄糖基-1-β-D-呋喃呋喃糖基氨基咪唑2'，3''，4''-三磷酸（7）和3'-O-α-D-吡喃葡萄糖基-9-beta的合成描述了-D-呋喃呋喃核糖嘌呤2'，3''，4''-三磷酸（8），这是超强1D-肌醇1,4,5-三磷酸受体激动剂腺苷A（2）的两个类似物。通过改进的路线由1,2-O-异亚丙基-α-D-木呋喃糖制备5-O-苄基-1，2-O-异亚丙基-α-D-呋喃核糖，并与3,4-di-O偶联-乙酰基-2,6-二-O-苄基-D-吡喃葡萄糖基二甲基亚磷酸酯得到3'，4'-二-O-乙酰基-2'，5，6'-三-O-苄基-3-O- α-D-吡喃葡萄糖基-1，2-O-异亚丙基-α-D-呋喃呋喃糖。除去异亚丙基缩醛并随后乙酰化得到中心二糖1,2,3'，4'-四-O-乙酰基-2'，5、6'-三-O-苄基-3-O-α-D-吡喃葡萄糖基-D-呋喃呋喃糖。用活化的咪唑或嘌呤进行弗布吕

  DOI：

  10.1021/jm000265o

文献信息

• Triazolophostins: a library of novel and potent agonists of IP₃receptors
  作者：Amol M. Vibhute、Vera Konieczny、Colin W. Taylor、Kana M. Sureshan

  DOI：10.1039/c5ob00440c

  日期：——

  IP₃R initiate most cellular Ca²⁺signaling. AdA is the most potent agonist of IP₃R. The structural complexity of AdA makes synthesis of its analogs cumbersome. We report an easy method for generating a library of potent triazole-based analogs of AdA, triazolophostins, which are the most potent AdA analogs devoid of a nucleobase.

  IP3R启动大多数细胞Ca2+信号传导。AdA是IP3R最有效的激动剂。AdA的结构复杂性使其类似物的合成繁琐。我们报告了一种简单的方法，用于生成一系列强效的基于三唑的AdA类似物库，即三唑磷酸酯，它们是最强效的AdA类似物，不含核碱基。
• 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.