Methyl 3,6-di-O-benzoyl-β-D-glucopyranoside | 51996-11-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 3,6-di-O-benzoyl-β-D-glucopyranoside
• CAS: 51996-11-3
• 化学式: C₂₁H₂₂O₈
• 分子量: 402.401
• InChiKey: WCYRUJGIOQEIFC-DKLJTFSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.16
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  111.52
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  苯甲酰氯 、 甲基 Β-D-吡喃葡萄糖苷 在 1-羟基苯并三唑 、 三乙胺 作用下， 生成 Methyl 3,6-di-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  Regioselective Acylation of Carbohydrates with 1-Acyloxy-1H-benzotriazoles

  摘要：

  代表性碳水化合物衍生物的酰化反应是通过原位生成的1-酰氧基-1H-苯并三唑完成的。所观察到的较高的位选择性、温和的反应条件和简便的后续处理使得所提出的单锅法具有普遍适用性，并且比之前引入的试剂（包括N-酰基咪唑）的酰化反应更具优势。

  DOI：

  10.1055/s-1991-26635

文献信息

• A green and convenient method for regioselective mono and multiple benzoylation of diols and polyols
  作者：Xiaoling Zhang、Bo Ren、Jiantao Ge、Zhichao Pei、Hai Dong

  DOI：10.1016/j.tet.2015.12.074

  日期：2016.2

  An efficient method for regioselective benzoylation of diols and polyols was developed. The benzoylation is catalyzed by only 0.2 equiv of benzoate anion in acetonitrile with the addition of a stoichiometric amount of benzoic anhydride under very mild condition, leading to high yields. Compared with all other methods, this method shows particular advantage in regioselective multiple benzoylation of polyols, and in avoiding the use of any metal-based catalysts and any amine bases, which is more environment friendly. (C) 2015 Elsevier Ltd. All rights reserved.
• Reagent-Dependent Regioselective Control in Multiple Carbohydrate Esterifications
  作者：Hai Dong、Zhichao Pei、Styrbjörn Byström、Olof Ramström

  DOI：10.1021/jo0620821

  日期：2007.2.1

  Regioselective control in organotin-mediated multiple acylation of carbohydrates is presented. The acylation reagent could be efficiently used to direct the product formation. Reagent-dependent thermodynamic and kinetic control and dynamic assistance mechanisms are suggested, resulting in the efficient preparation of building blocks that normally require many steps with traditional synthesis.