cyclohexyl 2,3,4,6-tetra-O-benzoyl-α-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-α-D-glucopyranoside
• 英文别名: cyclohexyl 2,3,4,6-O-tetrabenzoyl-α-D-glucopyranoside；cyclohexyl 2,3,4,6-tetra-O-benzoyl-D-glucopyranoside；cyclohexyl-(tetra-O-benzoyl-α-D-glucopyranoside)；Cyclohexyl-(tetra-O-benzoyl-α-D-glucopyranosid)；[(2R,3R,4S,5R,6S)-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-VWJQFIRJSA-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-α-D-glucopyranoside 在 甲醇 、 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-benzoylglucosyl bromide 在 氯仿 、 四氯化钛 、 silver(l) oxide 作用下， 生成 cyclohexyl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

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

  摘要：

  DOI：

  10.1021/ja01637a058

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。
• 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。
• GeCl₂·Dioxane–AgBF₄ Catalyzed Activation of Glycosyl Fluorides for Glycosylation
  作者：Qiuyu Zhu、Yu Tang、Biao Yu

  DOI：10.1021/acs.orglett.2c01146

  日期：2022.5.27

  catalytic glycosyl fluoride activation system using the GeCl2·dioxane–AgBF4 combination was developed, which involves a reversible activation of the anomeric C–F bond by a [Ge(II)–Cl]+ cation and a reversible chloride ion transfer between Ge(II) and glycosyl cations. This catalytic glycosylation system is easy to operate, proceeds at room temperature, and offers a broad scope of substrates.

  开发了一种使用 GeCl 2 ·二恶烷-AgBF 4组合的催化糖基氟化物活化系统，该系统涉及通过 [Ge(II)-Cl] +阳离子对异头 C-F 键的可逆活化和在它们之间的可逆氯离子转移。 Ge(II) 和糖基阳离子。这种催化糖基化系统易于操作，在室温下进行，并提供广泛的底物。
• Stereoselective glycosylations using benzoylated glucosyl halides with inexpensive promoters
  作者：Teiichi Murakami、Yukari Sato、Motonari Shibakami

  DOI：10.1016/j.carres.2008.03.019

  日期：2008.6

  Reactions of O-benzoylated glucopyranosyl halide (I, Br), isolated or generated in situ from per-benzoylated glucose (8a) and trimethylsilyl halide, with various alcohols were efficiently promoted by zinc halide (Cl, Br) or N-bromosuccinimide with a catalytic ZnI2 to give the corresponding 1,2- trans-beta-glucosides in good to high yields. When the anomeric halogenation of 8a was carried out in the presence of reactive alcohols, 1,2-cis-alpha-glucosides were selectively formed. (C) 2008 Elsevier Ltd. All rights reserved.