A Simple Solution to the Age Old Problem of Regioselective Functionalization of Guanine: First Practical Synthesis of Acyclic N9- and/or N7-Guanine Nucleosides Starting from N2,N9-Diacetylguanine
Тип публикации: Journal Article
Дата публикации: 1999-06-01
scimago Q2
wos Q1
БС1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
11674536
Organic Chemistry
Краткое описание
Regioselective alkylation of guanine, a long-lasting challenge, has been overcome by understanding the role of acids as catalyst in the coupling reaction of DAG (10) with OBDDA (11). The acid-catalyzed and noncatalyzed reactions of 10 with OBDDA which mainly give N(7) and N(9) isomers, respectively, appear to follow different mechanisms. The practical utility of the noncatalyzed reaction, which gives almost quantitative yields of N(9) derivatives, is demonstrated by synthesizing acylovir/gancyclovir in high yields.
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Singh D., Wani M. J., Kumar A. A Simple Solution to the Age Old Problem of Regioselective Functionalization of Guanine: First Practical Synthesis of Acyclic N9- and/or N7-Guanine Nucleosides Starting from N2,N9-Diacetylguanine // Journal of Organic Chemistry. 1999. Vol. 64. No. 13. pp. 4665-4668.
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Singh D., Wani M. J., Kumar A. A Simple Solution to the Age Old Problem of Regioselective Functionalization of Guanine: First Practical Synthesis of Acyclic N9- and/or N7-Guanine Nucleosides Starting from N2,N9-Diacetylguanine // Journal of Organic Chemistry. 1999. Vol. 64. No. 13. pp. 4665-4668.
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TY - JOUR
DO - 10.1021/jo982304y
UR - https://pubs.acs.org/doi/10.1021/jo982304y
TI - A Simple Solution to the Age Old Problem of Regioselective Functionalization of Guanine: First Practical Synthesis of Acyclic N9- and/or N7-Guanine Nucleosides Starting from N2,N9-Diacetylguanine
T2 - Journal of Organic Chemistry
AU - Singh, Dharmendra
AU - Wani, Mukesh J
AU - Kumar, Ashok
PY - 1999
DA - 1999/06/01
PB - American Chemical Society (ACS)
SP - 4665-4668
IS - 13
VL - 64
PMID - 11674536
SN - 0022-3263
SN - 1520-6904
ER -
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@article{1999_Singh,
author = {Dharmendra Singh and Mukesh J Wani and Ashok Kumar},
title = {A Simple Solution to the Age Old Problem of Regioselective Functionalization of Guanine: First Practical Synthesis of Acyclic N9- and/or N7-Guanine Nucleosides Starting from N2,N9-Diacetylguanine},
journal = {Journal of Organic Chemistry},
year = {1999},
volume = {64},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://pubs.acs.org/doi/10.1021/jo982304y},
number = {13},
pages = {4665--4668},
doi = {10.1021/jo982304y}
}
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Singh, Dharmendra, et al. “A Simple Solution to the Age Old Problem of Regioselective Functionalization of Guanine: First Practical Synthesis of Acyclic N9- and/or N7-Guanine Nucleosides Starting from N2,N9-Diacetylguanine.” Journal of Organic Chemistry, vol. 64, no. 13, Jun. 1999, pp. 4665-4668. https://pubs.acs.org/doi/10.1021/jo982304y.