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A novel method for the design and synthesis of an isonucleoside containing a 2-oxa-6-thiobicyclo-[3.2.0]heptane skeleton is described. 2,2-Dimethyl-1,3-dioxan-5-one 13 was converted into a dioxa-bicyclohexane derivative in six steps. After cleavage of the epoxide group with a thiol (thiophenol or PMB mercaptan), the resulting product was subjected to the Mitsunobu reaction in the presence of a nucleobase. The reaction proceeded via the migration of the thiosulfide groups and gave the desired isonucleoside derivatives. In the case of a phenyl sulfide derivative, radical desulfurization followed by deprotection gave 4'-substituted 2',3'-dideoxyisonucleosides. A PMB sulfide derivative, on the other hand, was converted into the corresponding dimesylate, which was then treated with mercury acetate and trifluoroacetic acid to remove the PMB group. The resulting thiol derivative was treated with DBU to give the desired isonucleoside constructed on a 2-oxa-6-thiobicyclo[3.2.0]heptane scaffold after deprotection. The optimized conformer of the isonucleoside was calculated using DFT at the B3LYP/6-31G** level and was compared with that of lamivudine using model compounds.

Titel:	Design and Synthesis of Isonucleosides Constructed on a 2-Oxa-6-thiabicyclo[3.2.0]heptane Scaffold
Autor/in / Beteiligte Person:	YOSHIMURA, Yuichi ; ASAMI, Kazuhiro ; IMAMICHI, Tomozumi ; OKUDA, Tomoko ; SHIRAKI, Kimiyasu ; TAKAHATA, Hiroki
Link:	E-Journal im Bestand der UB Hagen? View record from PASCAL Archive
Zeitschrift:	Journal of organic chemistry, Jg. 75 (2010), Heft 12, S. 4161-4171
Veröffentlichung:	Washington, DC: American Chemical Society, 2010
Medientyp:	academicJournal
Umfang:	print, 27 ref
ISSN:	0022-3263 (print)
Schlagwort:	Biochemistry, molecular biology, biophysics Biochimie, biologie moléculaire, biophysique Organic chemistry Chimie organique Sciences exactes et technologie Exact sciences and technology Chimie Chemistry Réactivité et mécanismes Reactivity and mechanisms Chimie des radicaux libres Free radicals chemistry Préparations et propriétés Preparations and properties Composés hétérocycliques Heterocyclic compounds Cycles à un ou plusieurs atomes o, s, se, te et leurs analogues condensés Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Cycles à plusieurs atomes n dans un même cycle, dans plusieurs cycles séparés et dans des cycles condensés Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Sciences biologiques et medicales Biological and medical sciences Sciences biologiques fondamentales et appliquees. Psychologie Fundamental and applied biological sciences. Psychology Biochimie analytique, structurale et metabolique Analytical, structural and metabolic biochemistry Acides nucléiques Nucleic acids Bases nucléiques, nucléotides Nucleic bases, nucleotides 1,8-Diazabicyclo[5.4.0]undéc-7-ène 1,8-Diazabicyclo[5.4.0]undec-7-ene Base nucléique Nucleic base Base nucleica Base purique Purine base Base púrica Benzènethiol Thiophenols Clivage Cleavage Clivaje Composé modèle Model compound Compuesto modelo Conformation Conformación Déprotection Deprotection Desprotección Dérivé de la purine Purine derivatives Purina derivado Dérivé de la pyrimidine Pyrimidine derivatives Pirimidina derivado Désulfuration Desulfurization Desulfuración Epoxyde Epoxide Epóxido Hétérocycle azote Nitrogen heterocycle Heterociclo nitrógeno Hétérocycle oxygène Oxygen heterocycle Heterociclo oxígeno Hétérocycle soufre Sulfur heterocycle Heterociclo azufre Lamivudine Lamivudina Mercure Acétate Mercury Acetate Mercurio Acetato Méthode fonctionnelle densité Density functional method Radical libre organique Organic free radical Radical libre orgánico Réaction Mitsunobu Mitsunobu reaction Reacción Mitsunobu Spirane Spiran Espirano Sulfure organique Organic sulfide Sulfuro orgánico Synthèse chimique Chemical synthesis Síntesis química Thiol Tiol Transposition chimique Chemical rearrangement Transposición química 1,3-Dioxane dérivé Acétique acide(trifluoro) Pentitol(1,4:3,5-dianhydro-2-désoxy-3-thio)
Sonstiges:	Nachgewiesen in: PASCAL Archive Sprachen: English Original Material: INIST-CNRS Document Type: Article File Description: text Language: English Author Affiliations: Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan ; Laboratory of Human Retrovirology, Applied and Development Research Program, National Institute of Allergy and Infectious Diseases at Frederick, Science Applications International Corporation-Frederick, Inc., Frederick, Maryland 21702, United States ; Department of Virology, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan Rights: Copyright 2015 INIST-CNRS ; CC BY 4.0 ; Sauf mention contraire ci-dessus, le contenu de cette notice bibliographique peut être utilisé dans le cadre d’une licence CC BY 4.0 Inist-CNRS / Unless otherwise stated above, the content of this bibliographic record may be used under a CC BY 4.0 licence by Inist-CNRS / A menos que se haya señalado antes, el contenido de este registro bibliográfico puede ser utilizado al amparo de una licencia CC BY 4.0 Inist-CNRS Notes: Analytical, structural and metabolic biochemistry ; Organic chemistry

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Design and Synthesis of Isonucleosides Constructed on a 2-Oxa-6-thiabicyclo[3.2.0]heptane Scaffold