Novel preparation of cis,cis-trisubstituted cyclopropane nucleosides
1
Laboratoire de Synthèse Organique, UPRES A CNRS 6011, Faculté des Sciences, Université du Maine, Avenue Olivier Messiaen, F-72085 Le Mans Cedex 9, France
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Publication type: Journal Article
Publication date: 1999-01-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Novel cyclopropane nucleosides, cis -2′, cis -3′-bis(hydroxymethyl)cyclopropyl thymine 4a and adenine 4b were synthesized. The stereoselective ring contraction of cyclobutyl bromohydrin 8 afforded cyclopropyl aldehyde 9 with a cis,cis configuration. After oxidation, conversion to amide and Hofmann's rearrangement, methyl carbamate 12 was obtained. Its basic hydrolysis yielded amine 13 , then the target molecules were obtained by construction of bases.
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Gauvry N., Huet F. Novel preparation of cis,cis-trisubstituted cyclopropane nucleosides // Tetrahedron. 1999. Vol. 55. No. 5. pp. 1321-1328.
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Gauvry N., Huet F. Novel preparation of cis,cis-trisubstituted cyclopropane nucleosides // Tetrahedron. 1999. Vol. 55. No. 5. pp. 1321-1328.
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RIS
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TY - JOUR
DO - 10.1016/S0040-4020(98)01120-X
UR - https://doi.org/10.1016/S0040-4020(98)01120-X
TI - Novel preparation of cis,cis-trisubstituted cyclopropane nucleosides
T2 - Tetrahedron
AU - Gauvry, Noëlle
AU - Huet, François
PY - 1999
DA - 1999/01/01
PB - Elsevier
SP - 1321-1328
IS - 5
VL - 55
SN - 0040-4020
SN - 1464-5416
ER -
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BibTex (up to 50 authors)
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@article{1999_Gauvry,
author = {Noëlle Gauvry and François Huet},
title = {Novel preparation of cis,cis-trisubstituted cyclopropane nucleosides},
journal = {Tetrahedron},
year = {1999},
volume = {55},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/S0040-4020(98)01120-X},
number = {5},
pages = {1321--1328},
doi = {10.1016/S0040-4020(98)01120-X}
}
Cite this
MLA
Copy
Gauvry, Noëlle, et al. “Novel preparation of cis,cis-trisubstituted cyclopropane nucleosides.” Tetrahedron, vol. 55, no. 5, Jan. 1999, pp. 1321-1328. https://doi.org/10.1016/S0040-4020(98)01120-X.