Synthesis of Chiral Acyclic Nucleosides by Sharpless Asymmetric Dihydroxylation: Access to Cidofovir and Buciclovir
Publication type: Journal Article
Publication date: 2018-11-23
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
30468383
Organic Chemistry
Abstract
An efficient method to construct chiral acyclic nucleosides via Sharpless asymmetric dihydroxylation of N-allylpyrimidines or N-alkenylpurines is reported. A range of chiral acyclic nucleosides with two adjacent hydroxyl groups present on the side chains could be produced in good yields (up to 97% yield) and excellent enantioselectivities (90-99% ee). The synthetic utility of the reaction was demonstrated by the catalytic asymmetric synthesis of ( S)-Cidofovir and ( R)-Buciclovir.
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Total citations:
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Citations from 2024:
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GOST
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Qin T. et al. Synthesis of Chiral Acyclic Nucleosides by Sharpless Asymmetric Dihydroxylation: Access to Cidofovir and Buciclovir // Journal of Organic Chemistry. 2018. Vol. 83. No. 24. pp. 15512-15523.
GOST all authors (up to 50)
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Qin T., Li J., Xie M., Gui-Rong Q., Guo H. Synthesis of Chiral Acyclic Nucleosides by Sharpless Asymmetric Dihydroxylation: Access to Cidofovir and Buciclovir // Journal of Organic Chemistry. 2018. Vol. 83. No. 24. pp. 15512-15523.
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TY - JOUR
DO - 10.1021/acs.joc.8b02442
UR - https://doi.org/10.1021/acs.joc.8b02442
TI - Synthesis of Chiral Acyclic Nucleosides by Sharpless Asymmetric Dihydroxylation: Access to Cidofovir and Buciclovir
T2 - Journal of Organic Chemistry
AU - Qin, Tao
AU - Li, Jian-Ping
AU - Xie, Mingsheng
AU - Gui-Rong, Qu
AU - Guo, Haiming
PY - 2018
DA - 2018/11/23
PB - American Chemical Society (ACS)
SP - 15512-15523
IS - 24
VL - 83
PMID - 30468383
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2018_Qin,
author = {Tao Qin and Jian-Ping Li and Mingsheng Xie and Qu Gui-Rong and Haiming Guo},
title = {Synthesis of Chiral Acyclic Nucleosides by Sharpless Asymmetric Dihydroxylation: Access to Cidofovir and Buciclovir},
journal = {Journal of Organic Chemistry},
year = {2018},
volume = {83},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/acs.joc.8b02442},
number = {24},
pages = {15512--15523},
doi = {10.1021/acs.joc.8b02442}
}
Cite this
MLA
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Qin, Tao, et al. “Synthesis of Chiral Acyclic Nucleosides by Sharpless Asymmetric Dihydroxylation: Access to Cidofovir and Buciclovir.” Journal of Organic Chemistry, vol. 83, no. 24, Nov. 2018, pp. 15512-15523. https://doi.org/10.1021/acs.joc.8b02442.