methyl 6'-O-butyryl-2,2',3,3',4',6-hexa-O-mesitoyl-β-lactoside | 141485-04-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6'-O-butyryl-2,2',3,3',4',6-hexa-O-mesitoyl-β-lactoside
• 英文别名: [(2R,3R,4S,5R,6R)-3-[(2S,3R,4S,5S,6R)-6-(butanoyloxymethyl)-3,4,5-tris[(2,4,6-trimethylbenzoyl)oxy]oxan-2-yl]oxy-6-methoxy-4,5-bis[(2,4,6-trimethylbenzoyl)oxy]oxan-2-yl]methyl 2,4,6-trimethylbenzoate
• CAS: 141485-04-3
• 化学式: C₇₇H₉₀O₁₈
• 分子量: 1303.55
• InChiKey: PPFNYFKYKWLNFI-WNRMALSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.35
• 重原子数：
  95.0
• 可旋转键数：
  20.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  221.02
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  methyl 6'-O-butyryl-2,2',3,3',4',6-hexa-O-mesitoyl-β-lactoside 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以87%的产率得到methyl 2,2',3,3',4',6-hexa-O-mesitoyl-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
• 作为产物：
  描述：

  2,4,6-三甲基苯甲酸 、 methyl 6'-O-butyryl-β-lactoside 在 三氟乙酸酐 作用下， 以 苯 为溶剂， 反应 2.0h， 以100%的产率得到methyl 6'-O-butyryl-2,2',3,3',4',6-hexa-O-mesitoyl-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