Efficient one-pot per-O-acetylation-thioglycosidation of native sugars, 4,6-O-arylidenation and one-pot 4,6-O-benzylidenation-acetylation of S-/O-glycosides catalyzed by Mg(OTf)2
Efficient one-pot per-O-acetylation-thioglycosidation of native sugars, 4,6-O-arylidenation and one-pot 4,6-O-benzylidenation-acetylation of S-/O-glycosides catalyzed by Mg(OTf)2
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DOI：
10.1039/c6ra23198e
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发表时间：
2016-01-01
期刊：
影响因子：
3.9
通讯作者：
Ghosh, Rina
中科院分区：
文献类型：
--
作者：
Mukherjee, Mana Mohan;Basu, Nabamita;Ghosh, Rina
据报道，使用 0.5 摩尔％的 Mg(OTf)(2) 作为非吸湿性、可回收催化剂，在无溶剂条件下对天然单糖和二糖进行连续一锅全 O-乙酰化-S-/O-糖苷化。 10 mol% Mg(OTf)(2) 催化糖苷和硫代糖苷与苯甲醛或对甲氧基苯甲醛二甲基缩醛进行区域有效 4,6-O-芳基化反应，以高产率生成相应的 4,6-O-芳基化产物。 Mg(OTf)(2) 还可以高产率地介导单糖和二糖苷和硫代糖苷的连续一锅苯亚甲基化-乙酰化。
A sequential one-pot per-O-acetylation-S-/O-gEycosidation of native mono and disaccharides under solvent free conditions using 0.5 mole% of Mg(OTf)(2) as a non-hygroscopic, recyclable catalyst is reported. RegioseEective 4,6-O-aryhdenation of glycosides and thioglycosides with benzaldehyde or p-methoxybenzaldehyde dimethyl acetal is catalyzed by 10 mole% of Mg(OTf)(2) to produce the corresponding 4,6-O-aryhdenated product in high yields. Mg(OTf)(2) can also mediate sequential one-pot benzyhdenation-acetylation of mono and disaccharide based glycosides and thioglycosides in high yield.