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Synthesis of diethyl 2-thioxo-1,2,3,4-tetrahydroand hexahydropyrimidine-5-phosphonates

✍ Scribed by Anastasia A. Fesenko; Dmitrii A. Cheshkov; Anatoly D. Shutalev

Book ID: 104056380
Publisher: Royal Society of Chemistry
Year: 2008
Tongue: English
Weight: 249 KB
Volume: 18
Category: Article
ISSN: 0959-9436
DOI: 10.1016/j.mencom.2008.01.019

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✦ Synopsis

The reaction of sodium enolate of diethyl (2-oxoprop-1-yl)phosphonate with N-(1-tosylprop-1-yl)thiourea results in the stereoselective formation of diethyl (4R*,5R*,6R*)-6-ethyl-4-hydroxy-4-methyl-2-thioxohexahydropyrimidine-5-phosphonate, which is transformed into diethyl 4-ethyl-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-phosphonate and diethyl (4R*,5S*,6R*)-4-ethyl-6-methyl-2-thioxohexahydropyrimidine-5-phosphonate by acid-catalysed dehydration and stereoselective reduction with NaBH 4 -CF 3 COOH, respectively.

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