Synthesis of a novel 1,2-dithianenucleoside via Pummerer-like reaction, followed by Vorbruggen glycosylation between a 1,2-dithiane derivative and uracilElectronic supplementary information (ESI) available: Experimental procedures and characterization data of all new compounds. CCDC 931650. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c3cc44848g

The novel 1,2-dithianenucleoside was designed as a hybrid type of modification between 4′-thioribonucleoside and altritol nucleoside. The desired compound, i.e. , 1-[(3 R ,4 R ,5 S ,6 R )-4,5-dihydroxy-6-hydroxymethyl-1,2-dithianyl]uracil ( 20 ), was prepared via the Pummerer-like reaction, followed by Vorbruggen glycosylation between an appropriately protected 1,2-dithiane derivative and silylated uracil. The novel 1,2-dithianenucleoside was synthesized via Pummerer-like reaction followed by Vorbruggen glycosylation between a 1,2-dithiane derivative and uracil.