Phosphoric acid mono-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-ylmethyl) ester | 145933-76-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Phosphoric acid mono-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-ylmethyl) ester
• 英文别名: [(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]methyl dihydrogen phosphate
• CAS: 145933-76-2
• 化学式: C₇H₁₅O₈P
• 分子量: 258.165
• InChiKey: LLDNIWZLVYJGBW-CQOGJGKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  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 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 50.0h， 生成 Phosphoric acid mono-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-ylmethyl) 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

文献信息

• Synthesis of C-fucopyranosyl analogs of GDP-L-fucose as inhibitors of fucosyltransferases
  作者：Juan I. Luengo、John G. Gleason

  DOI：10.1016/s0040-4039(00)60893-6

  日期：1992.11

  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.