Events The 11th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session a. General Organic Synthesis of the event The 11th International Electronic Conference on Synthetic Organic Chemistry

Published date

30 Nov, 2007

Citation

Anatoly D. Shutalev, Anastasia A. Fesenko, Synthesis of 5-(diethoxyphosphoryl)-substituted Hydrogenated Pyrimidine-2-thiones, in Proceedings of The 11th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2007, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-11-01328

Facebook

Twitter

Synthesis of 5-(diethoxyphosphoryl)-substituted Hydrogenated Pyrimidine-2-thiones

Anatoly D. Shutalev ¹

Anastasia A. Fesenko ¹

1. Department of Organic Chemistry, M.V.Lomonosov State Academy of Fine Chemical Technology, 119571 Moscow, Russian Federation

Abstract

The reaction of sodium enolate of diethyl (2-oxoprop-1-yl)phosphonate with N-(1-tosylprop-1-yl)thiourea results in a 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 NaBH4 - CF3COOH, respectively.

Keywords

b-oxophosphonates

a-tosyl-substituted thioureas

thioureidoalkylation

5-(diethoxyphosphoryl)-substituted hydrogenated pyrimidine-2-thiones

reduction

acyliminium cations

-1-(2’,3’,4’,6’-TETRA-O-ACETYL-β-D-GLUCOPYRANOSYL)-3-(4”,6”-DIARYLPYRIMIDINE-2”-YL)-THIOUREAS

-7α-Alkoxyestra-1,3,5(10)-trienes