methyl 2,2',3,3',4',6-hexa-O-acetyl-β-lactoside | 141485-00-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,2',3,3',4',6-hexa-O-acetyl-β-lactoside
• 英文别名: 2-3-6-2'-3'-4'-hexa-O-acetyl-β-methyl-D-lactoside；Gal2Ac3Ac4Ac(b1-4)b-Glc1Me2Ac3Ac6Ac；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-methoxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 141485-00-9
• 化学式: C₂₅H₃₆O₁₇
• 分子量: 608.551
• InChiKey: SQOSBJKGDMCWTC-RGOVMONESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  42
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  215
• 氢给体数：
  1
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 三氯乙腈 作用下， 以 乙腈 为溶剂， 生成 methyl 2,2',3,3',4',6-hexa-O-acetyl-β-lactoside
  参考文献：
  名称：

  短小芽孢杆菌固定化乙酰木聚糖酯酶催化全乙酰化二糖初级区域选择性脱保护

  摘要：

  在这项工作中，全乙酰化乳糖和相关化合物已被测试为高级中间底物，用于由来自短小芽孢杆菌的乙酰木聚糖酯酶 (AXE) 催化的酶促脱保护。特别是，我们提出了一种简单有效的酶促程序，以获得在“乳”碳水化合物的半乳糖苷部分的 C6' 位置仅带有一个游离伯羟基的产物。特别是，在 1-O-甲基乳糖胺和六乙酰乳醛的水解中取得了良好的产率（60-70%）。获得的产品作为用于合成非常重要的生物相关寡糖的高级构建模块引起了极大的兴趣。

  DOI：

  10.1002/ejoc.201100944

文献信息

• Application of protease-catalyzed regioselective esterification in synthesis of 6'-deoxy-6'-fluoro- and 6-deoxy-6-fluorolactosides
  作者：Shaopei Cai、Senitiroh Hakomori、Tatsushi Toyokuni

  DOI：10.1021/jo00038a036

  日期：1992.6

  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.