Synthesis of 3′-C-branched 1′,5′-anhydromannitol nucleosides as new antiherpes agents
Publication type: Journal Article
Publication date: 1998-03-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
A series of 3′-β-C-branched anhydromannitol nucleosides were conveniently synthesized starting from commercially available d -ribose. The reaction sequences were: (i) conversion of the protected pentofuranose to the corresponding nitrohexopyranose; (ii) addition of the conjugated base of the nitrosugar to formaldehyde; (iii) removal of the nitro group by n-tributyltin hydride treatment and (iv) Mitsunobu type alkylation to introduce the nucleobase. The conformation of intermediates and final compounds were deduced from NMR analysis. The thymine congener showed potent activity against herpes simplex virus (HSV).
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Hossain N. et al. Synthesis of 3′-C-branched 1′,5′-anhydromannitol nucleosides as new antiherpes agents // Tetrahedron. 1998. Vol. 54. No. 10. pp. 2209-2226.
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Hossain N., VAN HALBEEK H., De Clercq E., Herdewijn P. Synthesis of 3′-C-branched 1′,5′-anhydromannitol nucleosides as new antiherpes agents // Tetrahedron. 1998. Vol. 54. No. 10. pp. 2209-2226.
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RIS
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TY - JOUR
DO - 10.1016/s0040-4020(97)10431-8
UR - https://doi.org/10.1016/s0040-4020(97)10431-8
TI - Synthesis of 3′-C-branched 1′,5′-anhydromannitol nucleosides as new antiherpes agents
T2 - Tetrahedron
AU - Hossain, Nafizal
AU - VAN HALBEEK, HERMAN
AU - De Clercq, Erik
AU - Herdewijn, Piet
PY - 1998
DA - 1998/03/01
PB - Elsevier
SP - 2209-2226
IS - 10
VL - 54
SN - 0040-4020
SN - 1464-5416
ER -
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BibTex (up to 50 authors)
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@article{1998_Hossain,
author = {Nafizal Hossain and HERMAN VAN HALBEEK and Erik De Clercq and Piet Herdewijn},
title = {Synthesis of 3′-C-branched 1′,5′-anhydromannitol nucleosides as new antiherpes agents},
journal = {Tetrahedron},
year = {1998},
volume = {54},
publisher = {Elsevier},
month = {mar},
url = {https://doi.org/10.1016/s0040-4020(97)10431-8},
number = {10},
pages = {2209--2226},
doi = {10.1016/s0040-4020(97)10431-8}
}
Cite this
MLA
Copy
Hossain, Nafizal, et al. “Synthesis of 3′-C-branched 1′,5′-anhydromannitol nucleosides as new antiherpes agents.” Tetrahedron, vol. 54, no. 10, Mar. 1998, pp. 2209-2226. https://doi.org/10.1016/s0040-4020(97)10431-8.