2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-3-O-<(3R)-3-(tetradecanoyloxy)tetradecanoyl>-α-D-glucopyranosyl fluoride 4-(dihydrogen phosphate) | 138527-39-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-3-O-<(3R)-3-(tetradecanoyloxy)tetradecanoyl>-α-D-glucopyranosyl fluoride 4-(dihydrogen phosphate)
• 英文别名: [(2R,3R,4R,5S,6R)-2-fluoro-6-(hydroxymethyl)-3-[[(3R)-3-hydroxytetradecanoyl]amino]-5-phosphonooxyoxan-4-yl] (3R)-3-tetradecanoyloxytetradecanoate
• CAS: 138527-39-6
• 化学式: C₄₈H₉₁FNO₁₂P
• 分子量: 924.222
• InChiKey: DMSHXHBPCDSLRB-DMOHYYOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.5
• 重原子数：
  63
• 可旋转键数：
  44
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  198
• 氢给体数：
  5
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-3-O-<(3R)-3-(tetradecanoyloxy)tetradecanoyl>-α-D-glucopyranosyl fluoride 4-(diphenyl phosphate) 在 platinum(IV) oxide 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以97%的产率得到2-deoxy-2-<(3R)-3-hydroxytetradecanamido>-3-O-<(3R)-3-(tetradecanoyloxy)tetradecanoyl>-α-D-glucopyranosyl fluoride 4-(dihydrogen phosphate)
  参考文献：
  名称：

  2,6-二脱氧-6-氟-2-[（3R和3S）-3-羟基十四烷酰胺基] -3-O-[（3R）-3-（十四烷酰氧基）四癸酰基] -D-吡喃葡萄糖4-（磷酸二氢）和2-脱氧-2-[（（3R和3S）-3-羟基十四烷酰胺基] -3-O-[（3R）-3-（十四烷氧基）四癸酰基]-α-D-吡喃葡萄糖基氟化物4-（二氢磷酸盐）：GLA-60的氟糖类似物。

  摘要：

  Both 2,6-dideoxy-6-fluoro-2-[(3R)- and (3S)-3-hydroxytetradecanamido]-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glucopyranose 4-phosphate, 11 and 11' (6-fluoro GLA-60 and its 3'-epimer), and 2-deoxy-2[(3R)- and (3S)-(3-hydroxytetradecanamido]-3-O-[(3R)-3-(tetradecanoyloxy)tetradecanoyl]-alpha-D-glucopyranosyl fluoride 4-(dihydrogen phosphate), 18 and 18' (1-fluoro GLA-60 and its 3'-epimer), were synthesized from ally 2-deoxy-4,6-O-isopropylidene-2-trifluoroacetamido-alpha-D-glucopyranoside.

  DOI：

  10.1016/0008-6215(91)89008-4