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

, 
Dmitriy Aleksandrovich Cheshkov 1
Dmitriy Aleksandrovich Cheshkov
, 
Anatoly Dmitrievich Shutalev 1
Anatoly Dmitrievich Shutalev
10.1016/j.mencom.2008.01.019
Published 2008-01-14
Communication , Volume 18, Issue 1, 51-53
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Fesenko A. A., Cheshkov D. A., Shutalev A. D. Synthesis of diethyl 2-thioxo-1,2,3,4-tetrahydroand hexahydropyrimidine-5-phosphonates // Mendeleev Communications. 2008. Vol. 18. No. 1. pp. 51-53.
GOST all authors (up to 50) Copy
Fesenko A. A., Cheshkov D. A., Shutalev A. D. Synthesis of diethyl 2-thioxo-1,2,3,4-tetrahydroand hexahydropyrimidine-5-phosphonates // Mendeleev Communications. 2008. Vol. 18. No. 1. pp. 51-53.
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TY - JOUR
DO - 10.1016/j.mencom.2008.01.019
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2008.01.019
TI - Synthesis of diethyl 2-thioxo-1,2,3,4-tetrahydroand hexahydropyrimidine-5-phosphonates
T2 - Mendeleev Communications
AU - Fesenko, Anastasia Andreevna
AU - Cheshkov, Dmitriy Aleksandrovich
AU - Shutalev, Anatoly Dmitrievich
PY - 2008
DA - 2008/01/14
PB - Mendeleev Communications
SP - 51-53
IS - 1
VL - 18
ER -
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@article{2008_Fesenko,
author = {Anastasia Andreevna Fesenko and Dmitriy Aleksandrovich Cheshkov and Anatoly Dmitrievich Shutalev},
title = {Synthesis of diethyl 2-thioxo-1,2,3,4-tetrahydroand hexahydropyrimidine-5-phosphonates},
journal = {Mendeleev Communications},
year = {2008},
volume = {18},
publisher = {Mendeleev Communications},
month = {Jan},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2008.01.019},
number = {1},
pages = {51--53},
doi = {10.1016/j.mencom.2008.01.019}
}
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Fesenko, Anastasia Andreevna, et al. “Synthesis of diethyl 2-thioxo-1,2,3,4-tetrahydroand hexahydropyrimidine-5-phosphonates.” Mendeleev Communications, vol. 18, no. 1, Jan. 2008, pp. 51-53. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2008.01.019.

Abstract

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 NaBH4–CF3COOH, respectively.

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