Regioselective alkylation of the exocyclic nitrogen of adenine and adenosine by the Mitsunobu reaction
Publication type: Journal Article
Publication date: 2010-06-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
A novel synthetic route to N 6 -substitution of adenine is presented, employing the Mitsunobu reaction as the key step. A range of primary and secondary alcohols all coupled in very good to excellent yields within 30 min at 45 °C, offering a milder alternative to the traditional nucleophilic aromatic substitution of 6-chloropurine. The utility of this protocol is further demonstrated by its application to the syntheses of N 6 , N 9 -di-substituted adenines, including the potent and selective A 1 adenosine receptor agonist N 6 -cyclopentyladenosine.
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Total citations:
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Citations from 2024:
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(9.52%)
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GOST
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Fletcher S. Regioselective alkylation of the exocyclic nitrogen of adenine and adenosine by the Mitsunobu reaction // Tetrahedron Letters. 2010. Vol. 51. No. 22. pp. 2948-2950.
GOST all authors (up to 50)
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Fletcher S. Regioselective alkylation of the exocyclic nitrogen of adenine and adenosine by the Mitsunobu reaction // Tetrahedron Letters. 2010. Vol. 51. No. 22. pp. 2948-2950.
Cite this
RIS
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TY - JOUR
DO - 10.1016/j.tetlet.2010.03.103
UR - https://doi.org/10.1016/j.tetlet.2010.03.103
TI - Regioselective alkylation of the exocyclic nitrogen of adenine and adenosine by the Mitsunobu reaction
T2 - Tetrahedron Letters
AU - Fletcher, Steven
PY - 2010
DA - 2010/06/01
PB - Elsevier
SP - 2948-2950
IS - 22
VL - 51
SN - 0040-4039
SN - 1873-3581
ER -
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BibTex (up to 50 authors)
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@article{2010_Fletcher,
author = {Steven Fletcher},
title = {Regioselective alkylation of the exocyclic nitrogen of adenine and adenosine by the Mitsunobu reaction},
journal = {Tetrahedron Letters},
year = {2010},
volume = {51},
publisher = {Elsevier},
month = {jun},
url = {https://doi.org/10.1016/j.tetlet.2010.03.103},
number = {22},
pages = {2948--2950},
doi = {10.1016/j.tetlet.2010.03.103}
}
Cite this
MLA
Copy
Fletcher, Steven. “Regioselective alkylation of the exocyclic nitrogen of adenine and adenosine by the Mitsunobu reaction.” Tetrahedron Letters, vol. 51, no. 22, Jun. 2010, pp. 2948-2950. https://doi.org/10.1016/j.tetlet.2010.03.103.