2-phenylethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside | 1093681-07-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-phenylethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
• 英文别名: 1-O-(2-phenylethyl)-2,3,4,6-tetra-O-benzyl-D-glucopyranose
• CAS: 1093681-07-2
• 化学式: C₄₂H₄₄O₆
• 分子量: 644.808
• InChiKey: CGQVFPPCTWCYEJ-QBLDGPCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.94
• 重原子数：
  48.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  苯乙醇 、 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate 在 2-萘二硫醚 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以52%的产率得到
  参考文献：
  名称：

  Photo-induced glycosylation using a diaryldisulfide as an organo-Lewis photoacid catalyst

  摘要：

  几种受体与三氯乙酰亚胺供体进行光诱导糖基化反应，使用双(2-萘基)二硫化物作为有机路易斯光酸（LPA）催化剂，反应高效进行，得到相应的糖苷产率较高。

  DOI：

  10.1039/c9ob02674f

文献信息

• Metal-free glycosylation with glycosyl fluorides in liquid SO₂
  作者：Krista Gulbe、Jevgeņija Lugiņina、Edijs Jansons、Artis Kinens、Māris Turks

  DOI：10.3762/bjoc.17.78

  日期：——

  to covalently bind Lewis basic fluoride ions in a relatively stable fluorosulfite anion (FSO2−). Herein we report the application of liquid SO2 as a promoting solvent for glycosylation with glycosyl fluorides without any external additive. By using various temperature regimes, the method is applied for both armed and disarmed glucose and mannose-derived glycosyl fluorides in moderate to excellent yields

  液态SO 2是一种极性溶剂，可溶解共价和离子化合物。二氧化硫也具有路易斯酸性质，包括在一个相对稳定的fluorosulfite阴离子的能力共价结合路易斯碱性氟化物离子（FSO 2 - ）。在本文中，我们报道了液态SO 2作为促进剂用于糖基氟化物的糖基化而没有任何外部添加剂的应用。通过使用各种温度方案，该方法可用于中等和极高产率的武装和解除武装的葡萄糖和甘露糖衍生的糖基氟化物。一系列新戊酰基保护的O-和S-甘露糖苷，以及C的一个实例合成甘露糖苷以证明糖基受体的范围。通过19 F NMR光谱证实了在液体SO 2中与糖基氟糖基化的过程中，亚硫酸氢盐物质的形成。提出了通过溶剂分离的离子对进行的二氧化硫辅助的糖基化机制，而观察到的α，β-选择性是受底物控制的，并且取决于热力学平衡。
• GaCl3-catalyzed activation of alkynyl glycosides for the synthesis of O-glycosides
  作者：Jhillu S. Yadav、Nagendra N. Yadav、Manoj K. Gupta、Nikhil Srivastava、Basi V. Subba Reddy

  DOI：10.1007/s00706-013-1091-7

  日期：2014.3

  AbstractA catalytic amount of GaCl3 (5 mol%) was found to activate alkynyl glycosides effectively under mild reaction conditions to furnish a variety of O-glycosides in good yields with high β-selectivity. Graphical abstract

  摘要发现在适度的反应条件下催化量的GaCl 3（5mol％）有效地活化炔基糖苷，以高产率和高β选择性提供各种O-糖苷。 图形概要
• Photo-induced glycosylation using reusable organophotoacids
  作者：Ryosuke Iwata、Kanjiro Uda、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1039/c4cc04753b

  日期：——

  The glycosylation reactions of glycosyl trichloroacetimidates and several alcohols using an organophotoacid as an activator under photoirradiation proceeded smoothly to give the corresponding glycosides in high yields.

  糖基三氯乙酰亚胺和几种醇的糖基化反应，在光照条件下使用有机光酸作为活化剂进行，顺利进行，产率较高地得到相应的糖苷。
• Photo-induced glycosylation using the edible polyphenol curcumin
  作者：Satomi Goi、Hidenari Shigeta、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1039/d4ob00624k

  日期：——

  Photo-induced glycosylations of trichloroacetimidate donors and alcohols using an edible polyphenol, curcumin, were examined under visible photo-irradiation (470 nm). It was found, for the first time, that these glycosylations proceed smoothly under mild reaction conditions to give the corresponding glycosides in high yields. In addition, the present glycosylation method was applicable to a wide range

  在可见光照射（470 nm）下检查了使用可食用多酚姜黄素的三氯乙酰亚胺酯供体和醇的光诱导糖基化。首次发现这些糖基化反应在温和的反应条件下顺利进行，以高产率产生相应的糖苷。此外，本糖基化方法适用于广泛的三氯乙酰亚胺酯供体和醇受体，并且对糖基亚磷酸酯、磷酸酯、( N-苯基)三氟乙酰亚胺酯、氟化物、糖醛和硫代糖苷表现出较高的化学选择性。
• Formation of O-Glycosidic Linkages from 1-Hydroxy Sugars by Bismuth(III) Triflate-Catalyzed Dehydrative Glycosidation
  作者：Takashi Yamanoi、Ryo Inoue、Sho Matsuda、Kazuya Iwao、Yoshiki Oda、Akihiro Yoshida、Keita Hamasaki

  DOI：10.3987/com-08-s(f)41

  日期：——

  This paper describes the direct formation of various O-glycosidic linkages from 1-hydroxy sugars by bismuth(III) triflate-catalyzed dehydrative glycosidation. The condensation reactions of 1-hydroxy sugars with some primary alcohols in the presence of only 5 mol% bismuth(III) triflate at reflux temperature for 15 min in dichloromethane afforded O-glycosides in good yields. An 1,6-anhydro-beta-D-glucopyranosidic linkage was formed by the intramolecular condensation of the corresponding 1-hydroxy sugar performed with similar reaction conditions using 5 mol% bismuth(III) triflate. A reaction using 10 mol% bismuth(III) triflate at room temperature in dichloromethane promoted the self- or cross-condensations of I-hydroxy sugars to produce several kinds of 1,1'-disaccharides. This paper reports some important properties of bismuth(III) triflate catalyzed dehydrative glycosidation using 1-hydroxy sugars to form various O-glycosidic linkages.