1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside | 55628-56-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranose；[(2R,3R,4S,5R,6R)-2-acetyloxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 55628-56-3；65827-55-6；68567-54-4；77790-45-5；77790-46-6；81969-44-0；99630-89-4；125135-30-0；137567-77-2
• 化学式: C₃₁H₃₄O₈
• 分子量: 534.606
• InChiKey: SHXWXUTXYNDCRM-SAEUYMBFSA-N

物化性质

• 沸点：
  626.6±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  乙酸酐 、 ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 在 perchloric acid on silica gel 作用下， 反应 0.17h， 以90%的产率得到1,2-di-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Unprecedented Transformation of Thioglycosides to Their Corresponding 1‐O‐Acetates in the Presence of HClO₄‐SiO₂§

  摘要：

  An unprecedented conversion of thioalkyl/aryl glycoside to the corresponding 1-O-acetates has been described using acetic anhydride and HClO4-SiO2 at rt. Although this transformation does not play an important role in the oligosaccharide synthesis in comparison to its reverse transformation, this gives useful information in selecting the reaction condition for the synthesis of oligosaccharides. The yields were excellent in all cases.

  DOI：

  10.1080/07328300600860153

文献信息

• Tandem Epoxidation‐Alcoholysis or Epoxidation‐Hydrolysis of Glycals Catalyzed by Titanium(IV) Isopropoxide or Venturello’s Phosphotungstate Complex
  作者：Pieter Levecque、David W. Gammon、Henok Hadgu Kinfe、Pierre Jacobs、Dirk De Vos、Bert Sels

  DOI：10.1002/adsc.200800079

  日期：2008.7.7

  Venturello’s phosphotungstate complex and titanium(IV) isopropoxide [Ti(O-i-Pr)4] were successfully used as catalysts for the epoxidation-alcoholysis of glycals using hydrogen peroxide [H2O2]. Reaction substrates included a range of variously protected glycals and different alcohols were used as solvents. Ti(O-i-Pr)4 was only effective in methanol as solvent, but gave methyl glycosides in high yields

  Venturello的磷钨酸盐络合物和异丙醇钛（IV）[Ti（O- i- Pr）4 ]已成功用作使用过氧化氢[H 2 O 2 ]的环氧乙烷缩合醇解的催化剂。反应底物包括各种受保护的糖基，不同的醇用作溶剂。钛（O- i- Pr）4仅在甲醇作为溶剂中有效，但以高收率和高选择性得到甲基糖苷。事实证明，Ventrollo复合物是一种用途广泛且高效的催化剂。除了在醇类溶剂中进行环氧化-醇解以外，它还显示了在双相条件下的活性，以允许长链醇的糖基化，并且在苄基化的葡糖的立体选择性二羟基化中非常有效。
• Disaccharide-Containing Macrocycles by Click Chemistry and Intramolecular Glycosylation
  作者：Vinod K. Tiwari、Amit Kumar、Richard R. Schmidt

  DOI：10.1002/ejoc.201101815

  日期：2012.5

  with a triazolylmethyl moiety have been successfully employed as a relatively rigid spacer system in intramolecular glycosylation reactions. Phenyl 3,4,6-tri-O-benzyl-2-O-propargyl-1-thio-D-glucopyranoside was employed as a donor, which could be readily connected by 1,3-dipolar cycloaddition (click reaction) to O-(2- or 3-azidomethylbenzyl)-protected acceptors to afford, after liberation of the accepting

  在这项研究中，邻和间亚二甲苯基部分与三唑基甲基部分的组合已成功用作分子内糖基化反应中相对刚性的间隔系统。Phenyl 3,4,6-tri-O-benzyl-2-O-propargyl-1-thio-D-glucopyranoside 用作供体，它可以通过 1,3-偶极环加成（点击反应）很容易地连接到 O -(2- 或 3-叠氮甲基苄基)-保护的受体，在受体羟基释放后提供所需的供体-间隔基-受体连接的中间体。NIS/TMSOTf 促进的糖基化提供了含二糖的大环化合物。总的来说，获得了非常好的结果。异头选择性取决于各种因素，环大小似乎至关重要。
• An Efficient Stereoselective Dihydroxylation of Glycals using a Bimetallic System, RuCl₃/CeCl₃/NaIO₄
  作者：Pallavi Tiwari、Anup Kumar Misra

  DOI：10.1021/jo0526385

  日期：2006.3.31

  A catalytic dihydroxylation reaction on glycals has been developed using a bimetallic oxidizing system to furnish sugar 1,2-diols in a highly setreoselective manner.
• Stereoselective synthesis of α-glucosides by neighbouring group participation via an intermediate thiophenium ion
  作者：Daniel J. Cox、Antony J. Fairbanks

  DOI：10.1016/j.tetasy.2009.02.018

  日期：2009.5

  The use of a 2-O-(thiophen-2-yl)methyl protecting group allows highly stereoselective alpha-glucosylation of a trichloroacetimidate donor: increased stereoselectivity, presumably arising from the intramolecular formation of a transient intermediate thiophenium ion, correlates with increased bulk of the glycosyl acceptor. (C) 2009 Elsevier Ltd. All rights reserved.
• Crich, David; Lim, Linda B. L., Journal of the Chemical Society. Perkin transactions I, 1991, # 9, p. 2209 - 2214
  作者：Crich, David、Lim, Linda B. L.

  DOI：——

  日期：——