phenyl 2,3,4,6-tetra-O-benzoyl-1-sulfonyl-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenyl 2,3,4,6-tetra-O-benzoyl-1-sulfonyl-β-D-glucopyranoside
• 英文别名: phenylsulfonyl 2,3,4,6-tetra-O-benzoyl-1-deoxy-β-D-glucopyranoside；[(2R,3R,4S,5R,6S)-6-(benzenesulfonyl)-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• 化学式: C₄₀H₃₂O₁₁S
• 分子量: 720.753
• InChiKey: WDLQMXXOFMUUHG-VWJQFIRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  52
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  157
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 sodium methylate 、 过氧化脲素 作用下， 以 溶剂黄146 为溶剂， 反应 10.0h， 生成 phenyl 2,3,4,6-tetra-O-benzoyl-1-sulfonyl-β-D-glucopyranoside
  参考文献：
  名称：

  尿素-过氧化氢促使硫代糖苷选择性和受控地氧化为亚砜和砜。

  摘要：

  已经报道了使用脲-过氧化氢（UHP）将硫代糖苷选择性和控制地氧化为相应的糖基亚砜和砜的实用方法。在60°C下使用1.5当量的UHP选择性地获得了广泛的糖基亚砜，而在80°C下使用2.5当量的UHP在乙酸中实现了相应的砜。显着地，发现在硫化物的氧化过程中对氧化敏感的烯烃官能团是稳定的。

  DOI：

  10.3762/bjoc.13.113

文献信息

• Investigations into the Chemistry of Some 1,6-Epithio and 1,6-Episeleno ß-D-Glucopyranoses
  作者：Brian W. Skelton、Robert V. Stick、D. Matthew G. Tilbrook、Allan H. White、Spencer J. Williams

  DOI：10.1071/ch99164

  日期：——

  Derivatives of 1,6-dideoxy-1,6-epithio-β-D-glucopyranose have been shownto undergo oxidation reactions to afford the corresponding sulfoxides andsulfones. The sulfoxides participate in Pummerer reactions to afford thecorresponding α-acetoxy sulfides which were then oxidized further. Noneof the sulfoxides, sulfones or α-acetoxy sulfides prepared wereparticularly efficient glycosyl donors. Also presented

  1,6-二脱氧-1,6-环硫代-β-D-吡喃葡萄糖的衍生物已被证明会发生氧化反应以提供相应的亚砜和砜。亚砜参与Pummerer反应，得​​到相应的α-乙酰氧基硫化物，然后进一步氧化。制备的亚砜、砜或α-乙酰氧基硫化物都不是特别有效的糖基供体。还介绍了 1,6-dideoxy-1,6-epithio-β-D-glucopyranose S,S-dioxide 和 1,6-dideoxy-1,6-episeleno-β-D-glucopyranose 的晶体结构，有趣的类似物 1,6-脱水-β-D-吡喃葡萄糖。
• Fast oxidation of thioglycosides to glycosyl sulfones using KMnO4/CuSO4·5H2O under neutral reaction conditions
  作者：Geetanjali Agnihotri、Anup Kumar Misra

  DOI：10.1016/j.carres.2005.11.025

  日期：2006.2

  A rapid oxidation of thioglycosides to glycosyl sulfones has been achieved using a combination of KMnO4 and CuSO(4)center dot 5H(2)O in acetonitrile and water. This reaction protocol has many advantages compared to other methods available for this transformation, including compatibility with acid and base labile functional groups used for the protection of carbohydrates, high yields, fast reaction times, and moderate reaction temperatures. The yields obtained were excellent in all cases. (c) 2005 Elsevier Ltd. All rights reserved.
• Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones
  作者：Adesh Kumar Singh、Varsha Tiwari、Kunj Bihari Mishra、Surabhi Gupta、Jeyakumar Kandasamy

  DOI：10.3762/bjoc.13.113

  日期：——

  A practical method for the selective and controlled oxidation of thioglycosides to corresponding glycosyl sulfoxides and sulfones is reported using urea-hydrogen peroxide (UHP). A wide range of glycosyl sulfoxides are selectively achieved using 1.5 equiv of UHP at 60 °C while corresponding sulfones are achieved using 2.5 equiv of UHP at 80 °C in acetic acid. Remarkably, oxidation susceptible olefin

  已经报道了使用脲-过氧化氢（UHP）将硫代糖苷选择性和控制地氧化为相应的糖基亚砜和砜的实用方法。在60°C下使用1.5当量的UHP选择性地获得了广泛的糖基亚砜，而在80°C下使用2.5当量的UHP在乙酸中实现了相应的砜。显着地，发现在硫化物的氧化过程中对氧化敏感的烯烃官能团是稳定的。