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Novel azetidinones for carbapenems and fragmentation in the allylamine precursor analogue

Natalya Kazimirovna Selezneva 1
Natalya Kazimirovna Selezneva
, 
Zuleykha Rakhim'yanovna Valiullina 1
Zuleykha Rakhim'yanovna Valiullina
, 
Lidiya Semionovna Khasanova 1
Lidiya Semionovna Khasanova
, 
Fanuza Arslanovna Gimalova 1
Fanuza Arslanovna Gimalova
, 
Raisa Zigandarovna Biglova 1
Raisa Zigandarovna Biglova
, 
Mansur Sagar'yarovich Miftakhov 1
Mansur Sagar'yarovich Miftakhov
10.1016/j.mencom.2018.03.005
Published 2018-03-01
Communication , Volume 28, Issue 2, 131-132
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Selezneva N. K. et al. Novel azetidinones for carbapenems and fragmentation in the allylamine precursor analogue // Mendeleev Communications. 2018. Vol. 28. No. 2. pp. 131-132.
GOST all authors (up to 50) Copy
Selezneva N. K., Valiullina Z. R., Khasanova L. S., Gimalova F. A., Biglova R. Z., Miftakhov M. S. Novel azetidinones for carbapenems and fragmentation in the allylamine precursor analogue // Mendeleev Communications. 2018. Vol. 28. No. 2. pp. 131-132.
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TY - JOUR
DO - 10.1016/j.mencom.2018.03.005
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.03.005
TI - Novel azetidinones for carbapenems and fragmentation in the allylamine precursor analogue
T2 - Mendeleev Communications
AU - Selezneva, Natalya Kazimirovna
AU - Valiullina, Zuleykha Rakhim'yanovna
AU - Khasanova, Lidiya Semionovna
AU - Gimalova, Fanuza Arslanovna
AU - Biglova, Raisa Zigandarovna
AU - Miftakhov, Mansur Sagar'yarovich
PY - 2018
DA - 2018/03/01
PB - Mendeleev Communications
SP - 131-132
IS - 2
VL - 28
ER -
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@article{2018_Selezneva,
author = {Natalya Kazimirovna Selezneva and Zuleykha Rakhim'yanovna Valiullina and Lidiya Semionovna Khasanova and Fanuza Arslanovna Gimalova and Raisa Zigandarovna Biglova and Mansur Sagar'yarovich Miftakhov},
title = {Novel azetidinones for carbapenems and fragmentation in the allylamine precursor analogue},
journal = {Mendeleev Communications},
year = {2018},
volume = {28},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.03.005},
number = {2},
pages = {131--132},
doi = {10.1016/j.mencom.2018.03.005}
}
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Selezneva, Natalya Kazimirovna, et al. “Novel azetidinones for carbapenems and fragmentation in the allylamine precursor analogue.” Mendeleev Communications, vol. 28, no. 2, Mar. 2018, pp. 131-132. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.03.005.

Abstract

(2R,3R)-N-(3-Methoxy-2,3-dioxopropyl)-N-(4-methoxy-phenyl)-2,3-epoxybutanamide on treatment with strong bases (LDA, LHMDS) gives 3-[(1R)-1-hydroxyethyl]azetidin-2-one derivative, while the N-(3-methoxy-2-methylidene-3-oxo-propyl) analogue undergoes fragmentation.

References

1.
Comparative Review of the Carbapenems
Zhanel G.G., Wiebe R., Dilay L., Thomson K., Rubinstein E., Hoban D.J., Noreddin A.M., Karlowsky J.A.
Drugs, 2007
2.
Overcoming Resistance to β-Lactam Antibiotics
Worthington R.J., Melander C.
Journal of Organic Chemistry, 2013
4.
Enantioselective Syntheses of Carbapenem Antibiotics
Kametani T., Nagahara T.
Heterocycles, 1987
6.
Stereocontrolled syntheses of chiral intermediates of thienamycin from threonines
Shiozaki M., Ishida N., Hiraoka T., Yanagisawa H.
Tetrahedron Letters, 1981
9.
Enantiospecific synthesis of β-lactams via cycloaddition
Bose A.K., Manhas M.S., van der Veen J.M., Bari S.S., Wagle D.R., Hegde V.R., Krishnan L.
Tetrahedron Letters, 1985
10.
A new synthetic strategy for the penems. Total synthesis of (5R,6S,8R)-6-(.alpha.-hydroxyethyl)-2-(hydroxymethyl)penem-3-carboxylic acid
Hanessian S., Bedeschi A., Battistini C., Mongelli N.
Journal of the American Chemical Society, 1985
12.
Stereospecific synthesis of chiral precursors of thienamycin from L-threonine
Shiozaki M., Ishida N., Hiraoka T., Maruyama H.
Tetrahedron, 1984
13.
A Synthesis of a Versatile Intermediate Leading to Thienamycin Analogs
Maruyama H., Shiozaki M., Hiraoka T.
Bulletin of the Chemical Society of Japan, 1985
14.
Stereospecific Synthesis of D-Isothreonine from L-Threonine
Shimohigashi Y., Waki M., Izumiya N.
Bulletin of the Chemical Society of Japan, 1979
15.
A. B. Baylis and M. E. D. Hillman, German Patent 2155113, 1972.(Chem. Abstr., 1973, 77, 34174q).
17.
10.1016/j.mencom.2018.03.005_bib0045
Laurent
Eur. J. Org. Chem., 2006
21.
10.1016/j.mencom.2018.03.005_bib0065
Barluenga
Chem. Commun., 2005