Nucleic acid related compounds. 64. Synthesis of 2',3'-diazido-2',3'-dideoxyadenosine and 2',3'-diamino-2',3'-dideoxyadenosine from 9-(.beta.-D-arabinofuranosyl)adenine
Тип публикации: Journal Article
Дата публикации: 1991-05-01
scimago Q2
wos Q1
БС1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Краткое описание
Treatment of 9-(β-D-arabinofuranosyl) adenine (1) with triphenylphosphine and diethyl azodicarboxylate gave 9-(2,3-anhydro-β-D-lyxofuranosyl) adenine (2). Treatment of 2 with lithium azide and protection of the major product gave 9-[3-azido-5-O-(tert-butyldimethylsilyl)-3-deoxy-β-D-arabinofuranosyl] adenine (4). Trifluoromethanesulfonylation of 4 and treatment of the resulting triflate 5 with lithium azide gave 9-(5-O-TBDMS-2,3-diazido-2,3-dideoxy-β-D-ribofuranosyl) adenine (6). Deprotection of 6 gave 2',3'-diazido-2',3'-dideoxyadenosine (7), which was hydrogenated to give the secondary diamino nucleoside analogue, 2',3'-diamino-2',3'-dideoxyadenosine
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Chen Y. C. J. et al. Nucleic acid related compounds. 64. Synthesis of 2',3'-diazido-2',3'-dideoxyadenosine and 2',3'-diamino-2',3'-dideoxyadenosine from 9-(.beta.-D-arabinofuranosyl)adenine // Journal of Organic Chemistry. 1991. Vol. 56. No. 10. pp. 3410-3413.
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Chen Y. C. J., Hansske F., Janda K. D., Robins M. J. Nucleic acid related compounds. 64. Synthesis of 2',3'-diazido-2',3'-dideoxyadenosine and 2',3'-diamino-2',3'-dideoxyadenosine from 9-(.beta.-D-arabinofuranosyl)adenine // Journal of Organic Chemistry. 1991. Vol. 56. No. 10. pp. 3410-3413.
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TY - JOUR
DO - 10.1021/jo00010a042
UR - https://doi.org/10.1021/jo00010a042
TI - Nucleic acid related compounds. 64. Synthesis of 2',3'-diazido-2',3'-dideoxyadenosine and 2',3'-diamino-2',3'-dideoxyadenosine from 9-(.beta.-D-arabinofuranosyl)adenine
T2 - Journal of Organic Chemistry
AU - Chen, Y C Jack
AU - Hansske, Fritz
AU - Janda, Kim D.
AU - Robins, Morris J.
PY - 1991
DA - 1991/05/01
PB - American Chemical Society (ACS)
SP - 3410-3413
IS - 10
VL - 56
SN - 0022-3263
SN - 1520-6904
ER -
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@article{1991_Chen,
author = {Y C Jack Chen and Fritz Hansske and Kim D. Janda and Morris J. Robins},
title = {Nucleic acid related compounds. 64. Synthesis of 2',3'-diazido-2',3'-dideoxyadenosine and 2',3'-diamino-2',3'-dideoxyadenosine from 9-(.beta.-D-arabinofuranosyl)adenine},
journal = {Journal of Organic Chemistry},
year = {1991},
volume = {56},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/jo00010a042},
number = {10},
pages = {3410--3413},
doi = {10.1021/jo00010a042}
}
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MLA
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Chen, Y. C. Jack, et al. “Nucleic acid related compounds. 64. Synthesis of 2',3'-diazido-2',3'-dideoxyadenosine and 2',3'-diamino-2',3'-dideoxyadenosine from 9-(.beta.-D-arabinofuranosyl)adenine.” Journal of Organic Chemistry, vol. 56, no. 10, May. 1991, pp. 3410-3413. https://doi.org/10.1021/jo00010a042.