penta-O-acetyl-6'-O-butyryl-6-O-methyl-β-lactosyl fluoride | 141485-14-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: penta-O-acetyl-6'-O-butyryl-6-O-methyl-β-lactosyl fluoride
• 英文别名: butanoyl(-6)Gal2Ac3Ac4Ac(b1-4)b-Glc1F2Ac3Ac6Me；[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-fluoro-2-(methoxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl butanoate
• CAS: 141485-14-5
• 化学式: C₂₇H₃₉FO₁₆
• 分子量: 638.595
• InChiKey: ZVKRDWLJVLGXQS-YUYSRKNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  44
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  195
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  methyl 2,2',3,3',4'-penta-O-acetyl-6'-O-butyryl-β-lactoside 在 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以32%的产率得到methyl 2,2',3,3',4'-penta-O-acetyl-6'-O-butyryl-6-deoxy-6-fluoro-β-lactoside
  参考文献：
  名称：

  Application of protease-catalyzed regioselective esterification in synthesis of 6'-deoxy-6'-fluoro- and 6-deoxy-6-fluorolactosides

  摘要：

  Subtilisin-catalyzed esterification of methyl 4-O-beta-D-galactopyranosyl-beta-D-glucopyranoside (methyl beta-lactoside) (1) with 2,2,2-trichloroethyl butyrate (3) distinguished between the two primary hydroxyl groups of 1, yielding exclusively the 6'-O-monobutyryl derivative 6 from which 6'-deoxy-6'-fluoro- and 6-deoxy-6-fluorolactosides (22 and 29, respectively) were efficiently synthesized. A key feature in the synthesis of 22 was the use of the 2,4,6-trimethylbenzoyl (mesitoyl) group to protect the remaining free hydroxyl groups. A mesitoate ester, in addition to being inert to the condition that hydrolyzed a butyrate ester, could be easily cleaved by reduction with AlH3 without hydrogenolysis of a C-F bond. The steric bulk of a mesitoyl group suppressed the C-4' --> C-6' acyl migration during the fluorination with (diethylamino)sulfur trifluoride (DAST). The success in the synthesis of 29 depended on the choice of solvent employed for the DAST fluorination. With diglyme the desired 6-fluoro derivative 28 was the only product, whereas the use of CH2Cl2 yielded 6-O-methyl-beta-lactosyl fluoride 30 concomitantly through a C-1 --> C-6 migration of the methoxyl group.

  DOI：

  10.1021/jo00038a036