Acetic acid (3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(9H-xanthen-9-ylsulfanyl)-tetrahydro-pyran-3-yl ester | 497835-29-7

• 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: Acetic acid (3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(9H-xanthen-9-ylsulfanyl)-tetrahydro-pyran-3-yl ester
• 英文别名: [(2R,3S,4S,5R)-3,4,5-triacetyloxy-6-(9H-xanthen-9-ylsulfanyl)oxan-2-yl]methyl acetate
• CAS: 497835-29-7
• 化学式: C₂₇H₂₈O₁₀S
• 分子量: 544.579
• InChiKey: NKDHMLSSQSHFOU-UMPAEPOCSA-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：

  Acetic acid (3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(9H-xanthen-9-ylsulfanyl)-tetrahydro-pyran-3-yl ester 在 吡啶 、 4-二甲氨基吡啶 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 生成 Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-(9H-xanthen-9-ylsulfanyl)-tetrahydro-pyran-3-yl ester
  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：

  占吨醇 、 2,3,4,6-tetra-O-acetyl-1-thio-D-galactopyranoside 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 Acetic acid (3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(9H-xanthen-9-ylsulfanyl)-tetrahydro-pyran-3-yl ester
  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