Acetic acid (2R,3R,4R,5R,6S)-3,5-diacetoxy-2-hydroxymethyl-6-methyl-tetrahydro-pyran-4-yl ester | 145933-71-7

• 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-hydroxymethyl-6-methyl-tetrahydro-pyran-4-yl ester
• 英文别名: [(2S,3R,4R,5R,6R)-4,5-diacetyloxy-6-(hydroxymethyl)-2-methyloxan-3-yl] acetate
• CAS: 145933-71-7
• 化学式: C₁₃H₂₀O₈
• 分子量: 304.297
• InChiKey: AWLQFSNENKZMPF-WSBJEXOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4R,5R,6S)-3,5-diacetoxy-2-hydroxymethyl-6-methyl-tetrahydro-pyran-4-yl ester 在 platinum(IV) oxide 吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 50.0h， 生成 Acetic acid (2S,3R,4R,5R,6R)-3,5-diacetoxy-2-methyl-6-phosphonooxymethyl-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
• 作为产物：
  描述：

  Acetic acid (2R,3R,4R,5R,6S)-4,5-diacetoxy-2-(diethyl-methyl-silanyloxymethyl)-6-methyl-tetrahydro-pyran-3-yl ester 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到Acetic acid (2R,3R,4R,5R,6S)-3,5-diacetoxy-2-hydroxymethyl-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