Catalogo Articoli (Spogli Riviste)

OPAC HELP

Titolo:
Synthesis of bicyclic nucleosides by ring-closing metathesis
Autore:
Ravn, J; Nielsen, P;
Indirizzi:
Odense Univ, Dept Chem, Univ So Denmark, DK-5230 Odense M, Denmark Odense Univ Odense Denmark M Univ So Denmark, DK-5230 Odense M, Denmark
Titolo Testata:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
fascicolo: 9, , anno: 2001,
pagine: 985 - 993
SICI:
1472-7781(2001):9<985:SOBNBR>2.0.ZU;2-W
Fonte:
ISI
Lingua:
ENG
Soggetto:
NUCLEIC-ACID RECOGNITION; SUGAR-PHOSPHATE BACKBONE; CONSTRAINT CONFORMATIONAL FLEXIBILITY; BASE-PAIRING PROPERTIES; NMR COUPLING-CONSTANTS; OLEFIN METATHESIS; OLIGONUCLEOTIDE ANALOGS; SUBSTITUENT ELECTRONEGATIVITIES; CARBOCYCLIC THYMIDINE; ADENOSINE-DEAMINASE;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
58
Recensione:
Indirizzi per estratti:
Indirizzo: Nielsen, P Odense Univ, Dept Chem, Univ So Denmark, Campusvej 55, DK-5230 Odense M, Denmark Odense Univ Campusvej 55 Odense Denmark M 30 Odense M, Denmark
Citazione:
J. Ravn e P. Nielsen, "Synthesis of bicyclic nucleosides by ring-closing metathesis", J CHEM S P1, (9), 2001, pp. 985-993

Abstract

The ring-closing metathesis method is applied in the construction of conformationally restricted bicyclic nucleosides. From diacetone-D-glucose, the unsaturated bicyclic carbohydrate derivative 11 is efficiently obtained through two vinyl group Grignard additions, subsequent metathesis of the double bonds, and resolution of the stereochemistry by an oxidation/reduction reaction sequence. Two separate routes differing in the 3-O-protecting group are compared. Thus, an additional protecting step improves the yields significantly. Standard conversions of 11 give the bicyclic nucleoside 22 containing an olefinic moiety with a high potential for further functionalisation. As examples, two simple bicyclic ribo-nucleoside analogues 4 and 5, whichare restricted to the unusual South-type conformations, are synthesised.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 14/07/20 alle ore 05:18:51