Lázár László, Borbás Anikó, Somsák László
Department of Organic Chemistry, University of Debrecen, PO Box 400, H-4002, Hungary.
Department of Pharmaceutical Chemistry, University of Debrecen, PO Box 400, H-4002, Hungary.
Carbohydr Res. 2018 Dec;470:8-12. doi: 10.1016/j.carres.2018.09.005. Epub 2018 Sep 27.
Phenyl 2,3,6,2',3',6'-hexa-O-acetyl-4'-S-acetyl-1,4,4'-trithio-β-d-maltoside and its tri-, tetra- and pentasaccharide homologues were prepared by completely regio- and stereoselective photoinitiated thiol-ene coupling reactions of 2-acetoxy-glucal and 4-thioglucose type reaction partners. Complex protecting group strategies could be avoided since all thiols and glucals were prepared from a single starting material, phenyl 2,3,6-tri-O-acetyl-4-S-acetyl-1,4-dithio-β-d-glucopyranoside. The method represents a simple alternative to the known syntheses of similar products.
苯基 2,3,6,2',3',6'-六-O-乙酰基-4'-S-乙酰基-1,4,4'-三硫代-β-D-麦芽糖苷及其三糖、四糖和五糖同系物是通过 2-乙酰氧基葡糖醛和 4-硫代葡萄糖型反应伙伴的完全区域和立体选择性光引发硫醇-烯偶联反应制备的。由于所有硫醇和葡糖醛均由单一原料苯基 2,3,6-三-O-乙酰基-4-S-乙酰基-1,4-二硫代-β-D-吡喃葡萄糖苷制备，因此可以避免复杂的保护基策略。该方法是已知类似产物合成方法的一种简单替代方法。
