volume 24 issue 6 pages 1194-1198

An Economical Route to Lamivudine Featuring a Novel Strategy for Stereospecific Assembly

David R. Snead 1
D. Tyler McQuade 1
Saeed Ahmad 1
Rudy Krack 1
Rodger W. Stringham 1
Justina M Burns 1
Irini Abdiaj 1
Vijayagopal Gopalsamuthiram 1
Ryan C Nelson 1
B Frank Gupton 1
Publication typeJournal Article
Publication date2020-04-07
scimago Q1
wos Q1
SJR0.865
CiteScore5.4
Impact factor3.5
ISSN10836160, 1520586X
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
An economical synthesis of lamivudine was developed by employing a new method to establish the stereochemistry about the heterocyclic oxathiolane ring. Toward this end, an inexpensive and readily accessible lactic acid derivative served the dual purpose of activating the carbohydrate's anomeric center for N-glycosylation and transferring stereochemical information to the substrate simultaneously. Both enantiomers of the lactic acid derivative are available, and either β-enantiomer in this challenging class of 2'-deoxynucleoside active pharmaceutical ingredients can be formed.
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GOST Copy
Snead D. R. et al. An Economical Route to Lamivudine Featuring a Novel Strategy for Stereospecific Assembly // Organic Process Research and Development. 2020. Vol. 24. No. 6. pp. 1194-1198.
GOST all authors (up to 50) Copy
Snead D. R., McQuade D. T., Ahmad S., Krack R., Stringham R. W., Burns J. M., Abdiaj I., Gopalsamuthiram V., Nelson R. C., Gupton B. F. An Economical Route to Lamivudine Featuring a Novel Strategy for Stereospecific Assembly // Organic Process Research and Development. 2020. Vol. 24. No. 6. pp. 1194-1198.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1021/acs.oprd.0c00083
UR - https://doi.org/10.1021/acs.oprd.0c00083
TI - An Economical Route to Lamivudine Featuring a Novel Strategy for Stereospecific Assembly
T2 - Organic Process Research and Development
AU - Snead, David R.
AU - McQuade, D. Tyler
AU - Ahmad, Saeed
AU - Krack, Rudy
AU - Stringham, Rodger W.
AU - Burns, Justina M
AU - Abdiaj, Irini
AU - Gopalsamuthiram, Vijayagopal
AU - Nelson, Ryan C
AU - Gupton, B Frank
PY - 2020
DA - 2020/04/07
PB - American Chemical Society (ACS)
SP - 1194-1198
IS - 6
VL - 24
PMID - 32587454
SN - 1083-6160
SN - 1520-586X
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2020_Snead,
author = {David R. Snead and D. Tyler McQuade and Saeed Ahmad and Rudy Krack and Rodger W. Stringham and Justina M Burns and Irini Abdiaj and Vijayagopal Gopalsamuthiram and Ryan C Nelson and B Frank Gupton},
title = {An Economical Route to Lamivudine Featuring a Novel Strategy for Stereospecific Assembly},
journal = {Organic Process Research and Development},
year = {2020},
volume = {24},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021/acs.oprd.0c00083},
number = {6},
pages = {1194--1198},
doi = {10.1021/acs.oprd.0c00083}
}
MLA
Cite this
MLA Copy
Snead, David R., et al. “An Economical Route to Lamivudine Featuring a Novel Strategy for Stereospecific Assembly.” Organic Process Research and Development, vol. 24, no. 6, Apr. 2020, pp. 1194-1198. https://doi.org/10.1021/acs.oprd.0c00083.