1,6-anhydro-2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranose | 66963-55-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,6-anhydro-2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranose
• 英文别名: 1,6-anhydro-2-O-benzoyl-3,4-di-O-benzyl-beta-D-glucopyranose；[(1R,2R,3S,4R,5R)-2,3-bis(phenylmethoxy)-6,8-dioxabicyclo[3.2.1]octan-4-yl] benzoate
• CAS: 66963-55-1
• 化学式: C₂₇H₂₆O₆
• 分子量: 446.5
• InChiKey: PETMVJNSJPYEEE-ZANOAUCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranose 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 1,6-anhydro-3,4-di-O-benzyl-β-D-glucopyranose
  参考文献：
  名称：

  Anhydro-sugars

  摘要：

  该发明涉及新型1,6-脱水-β-D-己糖衍生物的公式I##STR1##其中R.sub.2是氢、甲基或芳香酰基，R.sub.3和R.sub.4是烷基、烯基或芳基烷基，其中R.sub.3和R.sub.4中的一个基团也是芳酰基，R.sub.4也可以是氢，但要求R.sub.3和R.sub.4的基团总共含有至少3个碳原子，并且如果R.sub.4是苄基基团，则基团R.sub.3含有至少2个碳原子，如果R.sub.3和R.sub.4中的一个基团是芳酰基，则R.sub.2是氢。这些化合物，尤其是1,6-脱水-3,4-二-O-苄基-β-D-葡萄糖吡喃糖或1,6-脱水-β-D-葡萄糖吡喃糖，可以用作纤溶剂和溶栓剂。

  公开号：

  US04177344A1
• 作为产物：
  描述：

  1,6-酸酐-2,3,4-三-O-苄基-β-D-吡喃葡萄糖 在 吡啶 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 生成 1,6-anhydro-2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of α-Glycosyl Thiols by Stereospecific Ring-Opening of 1,6-Anhydrosugars

  摘要：

  Treatment of 1,6-anhydrosugars with commercially available bis(trimethylsilyl) sulfide in the presence of trimethylsilyl triflate led to the formation of a-glycosyl thiols. All the reactions were highly stereoselective and afforded the a-glycosyl thiols in good to excellent yields. By this procedure, a variety of 1,6-anhydrosugars, differing in their sugar units, glycosidic linkages, and protecting group pattern, were converted smoothly into the corresponding a-glycosyl thiols, which could be of great utility in thioglycoside chemistry. It is noteworthy that 1,6-anhydrosugars carrying the 2-O-acyl group and 1,6-anhydrosugar-containing oligosaccharides could also be ring-opened stereospecifically under the same conditions to give rise to the corresponding 1-thiosugars in high yields. Thus, a very concise and efficient access to a-glycosyl thiols of great value was established.

  DOI：

  10.1021/jo202069y

文献信息

• Gold(I)-Catalyzed Glycosylation with Glycosyl<i>ortho</i>-Alkynylbenzoates as Donors: General Scope and Application in the Synthesis of a Cyclic Triterpene Saponin
  作者：Yao Li、Xiaoyu Yang、Yunpeng Liu、Cunsheng Zhu、You Yang、Biao Yu

  DOI：10.1002/chem.200902548

  日期：2010.2.8

  coupling with the poorly nucleophilic amides gives satisfactory yields. Moreover, excellent α‐selective glycosylation with a 2‐deoxy sugar donor and β‐selective sialylation have been realized. Application of the present glycosylation protocol in the efficient synthesis of a cyclic triterpene tetrasaccharide have further demonstrated the versatility and efficacy of this new method, in that a novel chemoselective

  糖基邻炔基苯甲酸酯已成为在金（I）配合物如Ph 3 PAuOTf和Ph 3 PAuNTf 2催化下进行糖苷化的新一代供体（Tf ＝三氟甲磺酸盐）。这些供体种类繁多，包括2-脱氧糖和唾液酸供体，易于制备且易于保存。与醇类的糖苷偶联收率通常非常好；即使与不良亲核酰胺直接偶联也能获得令人满意的收率。此外，已经实现了具有2-脱氧糖供体的出色的α-选择性糖基化和β-选择性唾液酸化。本糖基化方案在环状三萜四糖高效合成中的应用进一步证明了这种新方法的多功能性和有效性，因为已实现了羧酸的新型化学选择性糖基化和新的单锅顺序糖基化序列。
• Facile Preparation of 1,6-Anhydrohexoses using Solvent Effects and a Catalytic Amount of a Lewis Acid.
  作者：Per-Mikael Åberg、Beat Ernst、Erik De Clercq、Graciela Andrei、Robert Snoeck、Jan Balzarini、Bengt Fransson、Ulf Ragnarsson、George W. Francis

  DOI：10.3891/acta.chem.scand.48-0228

  日期：——

  Refluxing solutions of monosaccharides, unprotected at the 6-position and carrying O-methyl, S-ethyl, O-acetyl and OH-groups at the anomeric center, in acetonitrile containing a catalytic amount of a Lewis acid (O.1-0.4 equiv.) yielded 1,6-anhydrohexopyranoses in good to high yields. Best results were obtained with methyl 2,3,4-tri-O-dideuteriobenzyl-alpha-D-glycosides (87-91%). Dideuteriobenzyl protective

  在6位无保护并在端基中心带有O-甲基，S-乙基，O-乙酰基和OH-基团的单糖的回流溶液，在含有催化量路易斯酸（O.1-0.4当量。）以良好至高收率得到1,6-脱水己基吡喃糖。甲基2,3,4-三-O-二氘代苄基-α-D-糖苷（87-91％）获得了最佳结果。使用二异氘苄基保护基来促进NMR谱图的解释。
• Glycosyl Dioxalenium Ions as Reactive Intermediates of Automated Electrochemical Assembly
  作者：Akito Shibuya、Moeko Kato、Asuka Saito、Sujit Manmode、Naoto Nishikori、Toshiyuki Itoh、Aiichiro Nagaki、Toshiki Nokami

  DOI：10.1002/ejoc.202200135

  日期：2022.5.19

  Glycosyl dioxalenium ions generated from thioglycosides were used as observable reaction intermediates for automated electrochemical assembly of β-1,6-glucans. VT-NMR measurement revealed thermal stability of glycosyl dioxalenium ions and reaction temperature was rationally optimized based on information of their stability.

  由硫糖苷产生的糖基二氧杂二硫鎓离子被用作可观察到的反应中间体，用于 β-1,6-葡聚糖的自动电化学组装。VT-NMR测量揭示了糖基二氧戊二烯离子的热稳定性，并且基于它们的稳定性信息合理地优化了反应温度。
• Regioselective de-O-benzylation with Lewis acids
  作者：Hiroshi Hori、Yoshihiro Nishida、Hiroshi Ohrui、Hiroshi Meguro

  DOI：10.1021/jo00267a022

  日期：1989.3
• BASCHANG, G.;STANEK, J.;ROSSI, A.;SELE, A.
  作者：BASCHANG, G.、STANEK, J.、ROSSI, A.、SELE, A.

  DOI：——

  日期：——