volume 54 issue 10 pages 2209-2226

Synthesis of 3′-C-branched 1′,5′-anhydromannitol nucleosides as new antiherpes agents

Publication typeJournal Article
Publication date1998-03-01
scimago Q3
wos Q2
SJR0.426
CiteScore4.1
Impact factor2.2
ISSN00404020, 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).
Found 
Found 

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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.
GOST all authors (up to 50) Copy
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.
RIS |
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RIS Copy
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 -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@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}
}
MLA
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.