Acetic acid (2S,3S,4R,5R,6S)-3,5-diacetoxy-2-bromomethyl-6-methyl-tetrahydro-pyran-4-yl ester | 145933-73-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (2S,3S,4R,5R,6S)-3,5-diacetoxy-2-bromomethyl-6-methyl-tetrahydro-pyran-4-yl ester
• CAS: 145933-73-9
• 化学式: C₁₃H₁₉BrO₇
• 分子量: 367.194
• InChiKey: VBNVRQCFHIFGED-WSBJEXOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3S,4R,5R,6S)-3,5-diacetoxy-2-bromomethyl-6-methyl-tetrahydro-pyran-4-yl ester 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 (2,6-anhydro-1-deoxy-β-L-fuco-heptopyranosyl)phosphonic acid
  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 咪唑 、 溴 、 溶剂黄146 、 二苯基氯化膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 Acetic acid (2S,3S,4R,5R,6S)-3,5-diacetoxy-2-bromomethyl-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