Home / Publications / Synthesis of racemic Entecavir

Synthesis of racemic Entecavir

Nikolay Sergeyevich Vostrikov 1
Nikolay Sergeyevich Vostrikov
Ilya Fedorovich Lobko 1
Ilya Fedorovich Lobko
Zuleykha Rakhim'yanovna Valiullina 1
Zuleykha Rakhim'yanovna Valiullina
Mansur Sagar'yarovich Miftakhov 1
Mansur Sagar'yarovich Miftakhov
Published 2016-12-29
CommunicationVolume 27, Issue 1, 12-13
6
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Vostrikov N. S. et al. Synthesis of racemic Entecavir // Mendeleev Communications. 2016. Vol. 27. No. 1. pp. 12-13.
GOST all authors (up to 50) Copy
Vostrikov N. S., Lobko I. F., Valiullina Z. R., Miftakhov M. S. Synthesis of racemic Entecavir // Mendeleev Communications. 2016. Vol. 27. No. 1. pp. 12-13.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2017.01.002
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.01.002
TI - Synthesis of racemic Entecavir
T2 - Mendeleev Communications
AU - Vostrikov, Nikolay Sergeyevich
AU - Lobko, Ilya Fedorovich
AU - Valiullina, Zuleykha Rakhim'yanovna
AU - Miftakhov, Mansur Sagar'yarovich
PY - 2016
DA - 2016/12/29
PB - Mendeleev Communications
SP - 12-13
IS - 1
VL - 27
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2016_Vostrikov,
author = {Nikolay Sergeyevich Vostrikov and Ilya Fedorovich Lobko and Zuleykha Rakhim'yanovna Valiullina and Mansur Sagar'yarovich Miftakhov},
title = {Synthesis of racemic Entecavir},
journal = {Mendeleev Communications},
year = {2016},
volume = {27},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.01.002},
number = {1},
pages = {12--13},
doi = {10.1016/j.mencom.2017.01.002}
}
MLA
Cite this
MLA Copy
Vostrikov, Nikolay Sergeyevich, et al. “Synthesis of racemic Entecavir.” Mendeleev Communications, vol. 27, no. 1, Dec. 2016, pp. 12-13. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.01.002.

Abstract

Racemic Entecavir was prepared from Corey lactone diol benzylidene acetal in four steps in 24% overall yield.

References

1.
Synthesis and biological evaluation of 4-substituted fluoronucleoside analogs for the treatment of hepatitis B virus infection.
Yang Q., Kang J., Zheng L., Wang X., Wan N., Wu J., Qiao Y., Niu P., Wang S., Peng Y., Wang Q., Yu W., Chang J.
Journal of Medicinal Chemistry, 2015
2.
BMS-200475, a novel carbocyclic 2′-deoxyguanosine analog with potent and selective anti-hepatitis B virus activity in vitro
Bisacchi G.S., Chao S.T., Bachard C., Daris J.P., Innaimo S., Jacobs G.A., Kocy O., Lapointe P., Martel A., Merchant Z., Slusarchyk W.A., Sundeen J.E., Young M.G., Colonno R., Zahler R., et. al.
Bioorganic and Medicinal Chemistry Letters, 1997
3.
Identification of BMS-200475 as a potent and selective inhibitor of hepatitis B virus
Innaimo S.F., Seifer M., Bisacchi G.S., Standring D.N., Zahler R., Colonno R.J.
Antimicrobial Agents and Chemotherapy, 1997
4.
Entecavir
Scott L.J., Keating G.M.
Drugs, 2009
5.
Synthesis of Entecavir (BMS-200475)
Zhou B., Li Y.
Tetrahedron Letters, 2012
6.
A novel and efficient synthesis of Entecavir
Liu X., Jiao X., Wu Q., Tian C., Li R., Xie P.
Tetrahedron Letters, 2012
7.
Total Synthesis of Entecavir
Velasco J., Ariza X., Badía L., Bartra M., Berenguer R., Farràs J., Gallardo J., Garcia J., Gasanz Y.
Journal of Organic Chemistry, 2013
11.
Carbocyclic nucleoside analogues: classification, target enzymes, mechanisms of action and synthesis
12.
10.1016/j.mencom.2017.01.002_bib0025
Tolstikov
Zh. Org. Khim., 1984
13.
Alkoxy radical accelerated β-fragmentation of alcohols and lactols
Rigby J.H., Payen A., Warshakoon N.
Tetrahedron Letters, 2001
14.
Valiullina Z.R., Akhmet’yanova V.A., Vostrikov N.S., Miftakhov M.S.
Mendeleev Communications, 2016
15.
T.-C. Hu and H.-T. Huang, Patent US 20110201809 A1, 2011.
16.
D. Alberico, J. Clayton, C. Dixon and B. Gorin, Patent WO 2011150512 A1, 2011.
17.
D. Alberico, B. Gorin, R. Beharrilall, C. Dixon, J. Clayton and V. Rexon, Patent US 20130066071 A1, 2013.
18.
H. Kang and J. Chen, Faming Zhuanli Shenging, Patent CN 101693713 A2 0100414, 2010.
19.
Y. W. Ye, J. Yuan, J. Nie, D. Xu and C. Chen, Patent US 8937076 B2, 2015.
21.
Some solid state properties of enantiomers and their racemates
Chickos J.S., Garin D.L., Hitt M., Schilling G.
Tetrahedron, 1981
23.
Racemic sulprostone
Vostrikov N.S., Vasikov V.Z., Miftakhov M.S.
Russian Journal of Organic Chemistry, 2004
25.
10.1016/j.mencom.2017.01.002_sbref0050f
Navrátilová
Enantiomer, 2001