(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(9H-xanthen-9-ylsulfanyl)oxane-3,4,5-triol | 497835-21-9

• 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,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(9H-xanthen-9-ylsulfanyl)oxane-3,4,5-triol
• CAS: 497835-21-9
• 化学式: C₁₉H₂₀O₆S
• 分子量: 376.43
• InChiKey: NGTOWPHXWGULSJ-ILYVXUQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(9H-xanthen-9-ylsulfanyl)oxane-3,4,5-triol 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 生成 [(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-(9H-xanthen-9-ylsulfanyl)oxan-3-yl] 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
• 作为产物：
  描述：

  9-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]sulfanyl-9H-xanthene 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以79%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

文献信息

• The S -xanthenyl group: potential for application in the synthesis of thioglycosides
  作者：Robert A. Falconer

  DOI：10.1016/s0040-4039(02)02070-1

  日期：2002.11

  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.