[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(9H-xanthen-9-ylsulfanyl)oxan-2-yl]methyl acetate | 497835-20-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(9H-xanthen-9-ylsulfanyl)oxan-2-yl]methyl acetate
• CAS: 497835-20-8
• 化学式: C₂₇H₂₈O₁₀S
• 分子量: 544.579
• InChiKey: NKDHMLSSQSHFOU-NUPXYHBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  149
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(9H-xanthen-9-ylsulfanyl)oxan-2-yl]methyl acetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以91%的产率得到(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(9H-xanthen-9-ylsulfanyl)oxane-3,4,5-triol
  参考文献：
  名称：

  The S -xanthenyl group: potential for application in the synthesis of thioglycosides

  摘要：

  The S-xanthenyl (Xan) group was demonstrated to have potential as a convenient protecting group for 1-thiosugars in the synthesis of thioglycosides. Easily introduced by reaction of a 1-thiosugar with 9-hydroxyxanthene in the presence of catalytic TFA, the S-Xan group is compatible with a wide range of functionalities and protecting groups. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02070-1
• 作为产物：
  描述：

  (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(9H-xanthen-9-ylsulfanyl)oxane-3,4,5-triol 在 palladium on activated charcoal 吡啶 、 氢气 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(9H-xanthen-9-ylsulfanyl)oxan-2-yl]methyl acetate
  参考文献：
  名称：

  The S -xanthenyl group: potential for application in the synthesis of thioglycosides

  摘要：

  The S-xanthenyl (Xan) group was demonstrated to have potential as a convenient protecting group for 1-thiosugars in the synthesis of thioglycosides. Easily introduced by reaction of a 1-thiosugar with 9-hydroxyxanthene in the presence of catalytic TFA, the S-Xan group is compatible with a wide range of functionalities and protecting groups. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02070-1

文献信息

• Electrochemically Mediated S-Glycosylation of 1-Thiosugars with Xanthene Derivatives
  作者：Rui-Qi Wang、Qing-Hui Jiang、Hui-Xiang Wang、Xiao-Wei Zhang、Nan Yan

  DOI：10.1021/acs.orglett.3c01185

  日期：2023.6.16

  electrochemical dehydrogenative cross-coupling of benzylic C–H bonds with 1-thiosugars at room temperature is described. The direct S-glycosylation protocol avoids using any oxidant, which provides facile access to various glycosylated xanthene derivatives with up to 91% yield. This current electrooxidative reaction is characterized by high atom economy, high efficiency, mild reaction conditions, being

  描述了室温下苄基 C-H 键与 1-硫糖的有效电化学脱氢交叉偶联。直接 S-糖基化方案避免使用任何氧化剂，可以轻松获得各种糖基化呫吨衍生物，收率高达 91%。目前的电氧化反应具有原子经济性高、效率高、反应条件温和、环境友好、官能团耐受性好等特点。此外，初步的机理研究表明该反应涉及自由基过程。