✦ LIBER ✦

The synthesis and properties of new carbohydrate-modified mesoionic thiazolo[3,2-α]pyrimidine-5,7-dione acyclonucleosides

✍ Scribed by Daniel T. Stoelting; Godwin O. Mbagwu; Tina Scott; Michael Long; Elsa L. Sharpe

Publisher: Journal of Heterocyclic Chemistry
Year: 2002
Tongue: English
Weight: 63 KB
Volume: 39
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570390416

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✦ Synopsis

Abstract

The synthesis of the first examples of Class II mesoionic thiazolopyrimidine acyclonucleosides (MTA) incorporating the 2,3‐dihydroxypropyl moiety as the sugar simulator is described. First, 2‐bromothiazole was reacted with excess 1‐amino‐2,3‐propanediol acetonide via an aromatic nucleophilic substitution reaction to yield 1‐(2‐thiazolylamino)‐2,3‐propanediol acetonide. This acetonide intermediate was condensed at 160° with substituted bis(2,4,6‐trichlorophenyl) malonic esters to form a series of protected acyclonucleosides termed anhydro‐(8‐((2,2‐dimethyl‐1,3‐dioxolan‐4‐yl)methyl)‐5‐hydroxy‐7‐oxothiazolo[3,2‐a]pyrimi‐dinium hydroxides) which differ in their 6‐position substituent. Deprotection of these acyclonucleosides using p‐toluenesulfonic acid catalyst in methanol at 65° yielded the desired Class II MTA, anhydro‐(8‐(2,3‐dihydroxypropyl)‐5‐hydroxy‐7‐oxothiazolo[3,2‐a]pyrimidinium hydroxides).

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