Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-fluoro-6-tritylsulfanyl-tetrahydro-pyran-4-yl ester | 188540-57-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-fluoro-6-tritylsulfanyl-tetrahydro-pyran-4-yl ester
• CAS: 188540-57-0
• 化学式: C₃₁H₃₁FO₇S
• 分子量: 566.647
• InChiKey: JSFVXBRSAVKNSA-WYQCABFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-fluoro-6-tritylsulfanyl-tetrahydro-pyran-4-yl ester 在 吡啶 、 N-氯代丁二酰亚胺 、 Amberlite IRN 77 (H⁺ form) 、 硫化氢 、 sodium methylate 、 乙酸酐 作用下， 反应 12.0h， 生成
  参考文献：
  名称：

  Synthesis of 2-deoxy-2-fluoro-glucotropaeolin, a thioglucosidase inhibitor

  摘要：

  S(N)2-Displacement of the anomeric bromine atom in 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-alpha-D-glucopyranosyl bromide with the tetrabutylammonium salt of triphenylmethanethiol afforded the corresponding trityl 1-thio-beta-D-glucoside which led to the fully protected S-acetyl-2-fluoro-1-thio-beta-D-glucose derivative, and then to the free thiol 5 by selective S-deacetylation at low temperature. 2-Fluoro-glucotropaeolin (1) was obtained by a conventional procedure from 5. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00294-7
• 作为产物：
  描述：

  tetrabutylammonium salt of triphenylmethanethiol 、 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-α-D-glucopyranosyl bromide 以 甲苯 为溶剂， 以21%的产率得到Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-fluoro-6-tritylsulfanyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of 2-deoxy-2-fluoro-glucotropaeolin, a thioglucosidase inhibitor

  摘要：

  S(N)2-Displacement of the anomeric bromine atom in 3,4,6-tri-O-acetyl-2-deoxy-2-fluoro-alpha-D-glucopyranosyl bromide with the tetrabutylammonium salt of triphenylmethanethiol afforded the corresponding trityl 1-thio-beta-D-glucoside which led to the fully protected S-acetyl-2-fluoro-1-thio-beta-D-glucose derivative, and then to the free thiol 5 by selective S-deacetylation at low temperature. 2-Fluoro-glucotropaeolin (1) was obtained by a conventional procedure from 5. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00294-7