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

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 Vo...

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Veröffentlicht in:	Chemical communications (Cambridge, England) England), 2013-01, Vol.49 (71), p.7851-7853
Hauptverfasser:	Miyazawa, Tadashi, Umezaki, Kouhei, Tarashima, Noriko, Furukawa, Kazuhiro, Ooi, Takashi, Minakawa, Noriaki
Format:	Artikel
Sprache:	eng
Schlagworte:	Crystallography, X-Ray Glycosylation Molecular Conformation Quinolizines - chemistry Sulfur - chemistry Sulfur Compounds - chemistry Uracil - analogs & derivatives Uracil - chemical synthesis
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container_title	Chemical communications (Cambridge, England)
container_volume	49
creator	Miyazawa, Tadashi Umezaki, Kouhei Tarashima, Noriko Furukawa, Kazuhiro Ooi, Takashi Minakawa, Noriaki
description	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.
doi_str_mv	10.1039/c3cc44848g
format	Article
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subjects	Crystallography, X-Ray Glycosylation Molecular Conformation Quinolizines - chemistry Sulfur - chemistry Sulfur Compounds - chemistry Uracil - analogs & derivatives Uracil - chemical synthesis
title	Synthesis of a novel 1,2-dithianenucleoside via Pummerer-like reaction, followed by Vorbruggen glycosylation between a 1,2-dithiane derivative and uracil
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