allyl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside | 178319-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside
• 英文别名: allyl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranose；Bn(-2)[Bn(-6)]Glc3Ac4Ac(a)-O-allyl；[(2R,3R,4S,5R,6S)-4-acetyloxy-5-phenylmethoxy-2-(phenylmethoxymethyl)-6-prop-2-enoxyoxan-3-yl] acetate
• CAS: 178319-07-8
• 化学式: C₂₇H₃₂O₈
• 分子量: 484.546
• InChiKey: WYZGEERHHYVWOL-SEFGFODJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  allyl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside 在 palladium dihydroxide 吡啶 、 四氮唑 、 三甲基氯硅烷 、 4 A molecular sieve 、 氨 、 水 、 silver perchlorate 、 溶剂黄146 、 间氯过氧苯甲酸 、 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 、 水 、 乙二醇 、 甲苯 为溶剂， 反应 45.75h， 生成 Imidophostin
  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 2,6-di-O-benzyl-3-O-p-methoxybenzyl-α-D-galactopyranoside 在 吡啶 、 sodium hydroxide 、 2,3-dichloro-6,6-dicyano-1,4-benzoquinone 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.25h， 生成 allyl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  The Allyl Group for Protection in Carbohydrate Chemistry. XXXI. Conversion of Allyl 2,6-Di-O-benzyl-α-D-galactopyranoside Into Allyl 2,6-Di-O-benzyl-α-D-glucopyranoside and 2,6-Di-O-benzyl-D-glucopyranose

  摘要：

  烯丙基 2,6-二-O-苄基-α-D-吡喃半乳糖苷通过锡介导的烷基化反应转化为 3-O-对甲氧基苄基醚，从而得到 4-O-甲磺酰基衍生物。苯甲酸钠在回流的 N,N-二甲基甲酰胺中将最后一种化合物转化为 4-O-苯甲酰基-2,6-二-O-苄基-3-O-对甲氧基苄基-α-D-吡喃葡萄糖苷烯丙基，产量很高。将其皂化后，用 2,3-二氯-5,6-二氰基-1,4-苯醌处理产物，得到所需的烯丙基 2,6-二-O-苄基-α-D-吡喃葡萄糖苷，将其转化为已知的 2,3,4,6-四-O-苄基-D-吡喃葡萄糖，证实了其结构。通过标准程序从烯丙基 2,6-二-O-苄基-α-D-吡喃葡萄糖苷中去除烯丙基，得到 2,6-二-O-苄基-D-吡喃葡萄糖。这两种标题化合物都是合成 "腺苷 "类似物所需的中间体。

  DOI：

  10.1071/ch9960305

文献信息

• Contribution of the Adenine Base to the Activity of Adenophostin A Investigated Using a Base Replacement Strategy
  作者：Rachel D. Marwood、David J. Jenkins、Vanessa Correa、Colin W. Taylor、Barry V. L. Potter

  DOI：10.1021/jm000265o

  日期：2000.11.1

  pha-D-glucopyranosyl-D-ribofuranose. Vorbrüggen condensation with activated imidazole or purine gave the required beta-substituted derivatives which were further elaborated to 7 and 8, respectively. Radioligand binding assays to hepatic InsP(3) receptors and functional assays of Ca(2+) release from permeabilized hepatocytes gave a rank order of potency of the ligands 2 approximately 8 > 7 approximately

  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
• 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.