Acetic acid (2R,3R,4R,5R,6S)-3,5-diacetoxy-2-(2-hydroxy-ethyl)-6-methyl-tetrahydro-pyran-4-yl ester | 145987-59-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3R,4R,5R,6S)-3,5-diacetoxy-2-(2-hydroxy-ethyl)-6-methyl-tetrahydro-pyran-4-yl ester
• CAS: 145987-59-3
• 化学式: C₁₄H₂₂O₈
• 分子量: 318.324
• InChiKey: KPPNLQWEQAZUJL-OSHDJZDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.05
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  108.36
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4R,5R,6S)-3,5-diacetoxy-2-(2-hydroxy-ethyl)-6-methyl-tetrahydro-pyran-4-yl ester 在 platinum(IV) oxide 吡啶 、 氢气 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 50.0h， 生成 Phosphoric acid mono-[2-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yl)-ethyl] ester
  参考文献：
  名称：

  Synthesis of C-fucopyranosyl analogs of GDP-L-fucose as inhibitors of fucosyltransferases

  摘要：

  The syntheses of the C-fucopyranosyl analogs of GDP-L-fucose 2 - 5 as potential inhibitors of fucosyltransferases are reported. The synthetic routes are based on the C-glycosidation of tetra-O-acetyl-alpha-L-fucopyranose 6 under conditions that provided either beta- or alpha- C-fucosides with high stereoselectivity. Coupling to GMP was effected by Khorana's phosphomorpholidate method.

  DOI：

  10.1016/s0040-4039(00)60893-6
• 作为产物：
  描述：

  3-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-1-propene 在 sodium tetrahydroborate 、 臭氧 作用下， 生成 Acetic acid (2R,3R,4R,5R,6S)-3,5-diacetoxy-2-(2-hydroxy-ethyl)-6-methyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of C-fucopyranosyl analogs of GDP-L-fucose as inhibitors of fucosyltransferases

  摘要：

  The syntheses of the C-fucopyranosyl analogs of GDP-L-fucose 2 - 5 as potential inhibitors of fucosyltransferases are reported. The synthetic routes are based on the C-glycosidation of tetra-O-acetyl-alpha-L-fucopyranose 6 under conditions that provided either beta- or alpha- C-fucosides with high stereoselectivity. Coupling to GMP was effected by Khorana's phosphomorpholidate method.

  DOI：

  10.1016/s0040-4039(00)60893-6