Issue 71, 2013

Synthesis of a novel 1,2-dithianenucleoside via Pummerer-like reaction, followed by Vorbruggen glycosylation between a 1,2-dithiane derivative and uracil

Abstract

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-[(3R,4R,5S,6R)-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.

Graphical abstract: Synthesis of a novel 1,2-dithianenucleoside via Pummerer-like reaction, followed by Vorbruggen glycosylation between a 1,2-dithiane derivative and uracil

Supplementary files

Article information

Article type
Communication
Submitted
28 Jun 2013
Accepted
05 Jul 2013
First published
05 Jul 2013

Chem. Commun., 2013,49, 7851-7853

Synthesis of a novel 1,2-dithianenucleoside via Pummerer-like reaction, followed by Vorbruggen glycosylation between a 1,2-dithiane derivative and uracil

T. Miyazawa, K. Umezaki, N. Tarashima, K. Furukawa, T. Ooi and N. Minakawa, Chem. Commun., 2013, 49, 7851 DOI: 10.1039/C3CC44848G

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