Synthesis of 8-(ω-Hydroxyalkyl)-, 8-(ω-Hydroxyalk-1-enyl)-, and 8-(ω-Hydroxyalk-1-ynyl)adenines Using the tert-Butyldimethylsilyloxymethyl Group, a New and Versatile Protecting Group of Adenine
Тип публикации: Journal Article
Дата публикации: 2000-10-21
SCImago Q2
WOS Q1
БС1
SJR: 0.604
CiteScore: 5.8
Impact factor: 3.3
ISSN: 00223263, 15206904
PubMed ID:
11073587
Organic Chemistry
Краткое описание
The synthesis of 12 analogues of adenine substituted at C-8 by an ω-hydroxyalkyl, ω-hydroxyalk-1-enyl, or ω-hydroxyalk-1-ynyl chain of various length has been carried out in five or six steps starting from adenine. The analogues were obtained using a new protecting group of adenine, the tert-butyldimethylsilyloxymethyl group. 9-tert-Butyldimethylsilyloxymethyl-adenine is more soluble than adenine in organic solvents. It was prepared regiospecificaly in two steps from adenine and was amenable to C-8 iodination under basic conditions and to subsequent introduction of the various carbon chains at C-8 by palladium-catalyzed cross-coupling reactions (Stille or Sonogashira). The protecting group was removed under acidic conditions, thus demonstrating its versatility.
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Lang P. et al. Synthesis of 8-(ω-Hydroxyalkyl)-, 8-(ω-Hydroxyalk-1-enyl)-, and 8-(ω-Hydroxyalk-1-ynyl)adenines Using the tert-Butyldimethylsilyloxymethyl Group, a New and Versatile Protecting Group of Adenine // Journal of Organic Chemistry. 2000. Vol. 65. No. 23. pp. 7825-7832.
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Lang P., Magnin G., Mathis G., Burger A., Biellmann J. Synthesis of 8-(ω-Hydroxyalkyl)-, 8-(ω-Hydroxyalk-1-enyl)-, and 8-(ω-Hydroxyalk-1-ynyl)adenines Using the tert-Butyldimethylsilyloxymethyl Group, a New and Versatile Protecting Group of Adenine // Journal of Organic Chemistry. 2000. Vol. 65. No. 23. pp. 7825-7832.
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TY - JOUR
DO - 10.1021/jo000841o
UR - https://pubs.acs.org/doi/10.1021/jo000841o
TI - Synthesis of 8-(ω-Hydroxyalkyl)-, 8-(ω-Hydroxyalk-1-enyl)-, and 8-(ω-Hydroxyalk-1-ynyl)adenines Using the tert-Butyldimethylsilyloxymethyl Group, a New and Versatile Protecting Group of Adenine
T2 - Journal of Organic Chemistry
AU - Lang, Pascal
AU - Magnin, Geraldine
AU - Mathis, Gérald
AU - Burger, Alain
AU - Biellmann, Jean-François
PY - 2000
DA - 2000/10/21
PB - American Chemical Society (ACS)
SP - 7825-7832
IS - 23
VL - 65
PMID - 11073587
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (до 50 авторов)
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@article{2000_Lang,
author = {Pascal Lang and Geraldine Magnin and Gérald Mathis and Alain Burger and Jean-François Biellmann},
title = {Synthesis of 8-(ω-Hydroxyalkyl)-, 8-(ω-Hydroxyalk-1-enyl)-, and 8-(ω-Hydroxyalk-1-ynyl)adenines Using the tert-Butyldimethylsilyloxymethyl Group, a New and Versatile Protecting Group of Adenine},
journal = {Journal of Organic Chemistry},
year = {2000},
volume = {65},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://pubs.acs.org/doi/10.1021/jo000841o},
number = {23},
pages = {7825--7832},
doi = {10.1021/jo000841o}
}
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MLA
Скопировать
Lang, Pascal, et al. “Synthesis of 8-(ω-Hydroxyalkyl)-, 8-(ω-Hydroxyalk-1-enyl)-, and 8-(ω-Hydroxyalk-1-ynyl)adenines Using the tert-Butyldimethylsilyloxymethyl Group, a New and Versatile Protecting Group of Adenine.” Journal of Organic Chemistry, vol. 65, no. 23, Oct. 2000, pp. 7825-7832. https://pubs.acs.org/doi/10.1021/jo000841o.
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