cyclohexyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside | 6899-46-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cyclohexyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-cyclohexyloxyoxan-2-yl]methyl benzoate
• CAS: 6899-46-3
• 化学式: C₄₀H₃₈O₁₀
• 分子量: 678.736
• InChiKey: VEXOAISNTOJFQS-ZNNRSBSUSA-N

物化性质

• 熔点：
  177-178 °C
• 沸点：
  776.4±60.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  50
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  cyclohexyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside 在 甲醇 、 氯仿 、 四氯化钛 、 barium methoxide 作用下， 生成 环己基葡萄糖苷
  参考文献：
  名称：

  The Rearrangement of Acetylated and Benzoylated β-Glucosides Catalyzed by Titanium Tetrachloride²

  摘要：

  DOI：

  10.1021/ja01637a058
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl bromide 在 2,6-二甲基吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 生成 cyclohexyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  基于衍生自硒代糖苷的高反应性β-溴代糖苷的寡糖合成新的迭代策略。

  摘要：

  在不存在糖基受体的情况下将硒代糖苷立体选择性转化为β-溴代糖苷，然后与另一种硒代糖苷偶联，得到相应的糖基化硒代糖苷，其可直接用于下一个糖基化。该序列的迭代使得可以合成包括引发剂活性七糖在内的多种寡糖。[反应：看文字]

  DOI：

  10.1021/ol016713j

文献信息

• Direct Dehydrative Glycosylation Catalyzed by Diphenylammonium Triflate
  作者：Mei-Yuan Hsu、Sarah Lam、Chia-Hui Wu、Mei-Huei Lin、Su-Ching Lin、Cheng-Chung Wang

  DOI：10.3390/molecules25051103

  日期：——

  dehydrative glycosylations of carbohydrate hemiacetals catalyzed by diphenylammonium triflate under microwave irradiation are described. Both armed and disarmed glycosyl-C1-hemiacetal donors were efficiently glycosylated in moderate to excellent yields without the need for any drying agents and stoichiometric additives. This method has been successfully applied to a solid-phase glycosylation.

  描述了在微波辐射下由三氟甲磺酸二苯基铵催化的碳水化合物半缩醛的直接脱水糖基化的方法。武装和解除武装的糖基-C1-半缩醛供体均以中等至优异的产率有效糖基化，无需任何干燥剂和化学计量添加剂。该方法已成功应用于固相糖基化。
• Glycosylation with Disarmed Glycosyl Bromides Promoted by Iodonium Ions
  作者：Gyrithe Lanz、Robert Madsen

  DOI：10.1002/ejoc.201600545

  日期：2016.6

  Iodonium ions have been developed for activating glycosyl bromides in the coupling to glycosyl acceptors. The iodonium ions are generated from N-iodosuccinimide and a protic acid such as camphorsulfonic acid or triflic acid, where the latter gives the most reactive promoter system. The couplings occur with the release of iodine monobromide, and the best results are obtained with benzoylated glycosyl

  碘鎓离子已被开发用于激活与糖基受体偶联的糖基溴化物。碘鎓离子由 N-碘代琥珀酰亚胺和质子酸（如樟脑磺酸或三氟甲磺酸）产生，其中后者提供最具反应性的促进剂系统。偶联随着一溴化碘的释放而发生，使用苯甲酰化糖基供体和受体获得最佳结果。通过这种方式，去武装的糖基溴化物可以作为糖基供体，而无需使用重金属盐。
• Ionic Liquid [bmim]PF₆-Mediated Synthesis of 1,2-Orthoesters of Carbohydrates and the Glycosidation Reactions of 4-Pentenyl Orthoesters
  作者：Saithalavi Anas、Valiyaveetil Sanjayan Sajisha、Rani Rajan、Rajasekaran Thirumalai Kumaran、Kokkuvayil Vasu Radhakrishnan

  DOI：10.1246/bcsj.80.553

  日期：2007.3.15

  A facile synthesis of the 1,2-orthoesters of carbohydrates in the ionic liquid [bmim]PF6 without a quaternary ammonium salt like tetrabutylammonium iodide, is described. The glycosidation reactions of 4-pentenyl orthoesters (NPOEs) with different alcohols are also discussed. The work described in this paper showed that [bmim]PF6 is an efficient and recyclable solvent for the synthesis and glycosidation reaction of orthoesters.

  描述了一种在离子液体[bmim]PF6中合成糖类1,2-邻醚的简便方法，无需使用四丁基氨铵盐如碘化四丁基铵。还讨论了4-戊烯基邻醚（NPOEs）与不同醇的糖苷化反应。本文所述的工作表明，[bmim]PF6是一种高效且可回收的溶剂，用于邻醚的合成和糖苷化反应。
• Glycosylation with telluroglycosides. Stereoselective construction of α- and β-anomers
  作者：Shigeru Yamago、Koji Kokubo、Hideo Murakami、Yosuke Mino、Osamu Hara、Jun-ichi Yoshida

  DOI：10.1016/s0040-4039(98)01753-5

  日期：1998.10

  Telluroglycosides are activated under neutral conditions and serve as excellent glycosyl donors in the glycosylation reaction. Both α- and β-anomers are selectively formed by the proper choice of the C-2 protecting group and solvent.

  碲糖苷在中性条件下被激活，并在糖基化反应中充当出色的糖基供体。两个α-和β端基异构体是由C-2保护基，溶剂的适当选择有选择地形成。
• DISAL glycosyl donors for efficient glycosylations under acidic conditions: Application to solid-phase oligosaccharide synthesis
  作者：Lars Petersen、Knud J. Jensen

  DOI：10.1039/b105872j

  日期：——

  The use of DISAL (methyl dinitrosalicylate) glycosyl donors in efficient Lewis acid-promoted glycosylations is reported. N-Acetyl-D-glucosamine monosaccharide acceptors are successfully glycosylated at O-6 or O-4 using benzyl- and benzoyl-protected DISAL donors in CH2Cl2 or nitromethane in the presence of LiClO4. The resultant disaccharides are isolated in yields ranging from 35 to 93%. Other Lewis acids such as FeCl3, TMSOTf, or BF3·Et2O also prove efficient for glycosylation of the secondary alcohol cyclohexanol. However, for the synthesis of disaccharides, the mild activation by LiClO4 gives higher yields. This approach is extended to efficient solid-phase glycosylation of a D-glucosamine derivative anchored by the 2-amino group through a Backbone Amide Linker (BAL) to a polystyrene support.

  报告了在高效的路易斯酸促进糖基化反应中使用 DISAL（二硝基水杨酸甲酯）糖基供体的情况。在 CH2Cl2 或硝基甲烷中，在 LiClO4 的存在下，使用苄基和苯甲酰基保护的 DISAL 给体成功地在 O-6 或 O-4 处糖基化了 N-乙酰基-D-氨基葡萄糖单糖受体。由此分离出的二糖收率在 35% 到 93% 之间。其他路易斯酸（如 FeCl3、TMSOTf 或 BF3-Et2O）也被证明能有效地对仲醇环己醇进行糖基化。不过，在合成二糖时，LiClO4 的温和活化可获得更高的产量。这种方法扩展到了通过骨架酰胺连接物（BAL）将 2-氨基锚定在聚苯乙烯支架上的 D-氨基葡萄糖衍生物的高效固相糖基化。