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Titolo:
Oligonucleosides with a nucleobase-including backbone - Part 2 - Synthesisand structure determination of adenosine-derived monomers
Autore:
Gunji, H; Vasella, A;
Indirizzi:
ETH Zentrum, Organ Chem Lab, CH-8092 Zurich, Switzerland ETH Zentrum Zurich Switzerland CH-8092 Lab, CH-8092 Zurich, Switzerland
Titolo Testata:
HELVETICA CHIMICA ACTA
fascicolo: 7, volume: 83, anno: 2000,
pagine: 1331 - 1345
SICI:
0018-019X(2000)83:7<1331:OWANB->2.0.ZU;2-7
Fonte:
ISI
Lingua:
ENG
Soggetto:
ANTI DYNAMIC EQUILIBRIUM; PURINE NUCLEOSIDES; NUCLEOTIDES; NMR; DERIVATIVES; ANALOGS; 8-BROMO-2',3'-O-ISOPROPYLIDENEADENOSINE; CONFORMATIONS; LITHIATION; AID;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
34
Recensione:
Indirizzi per estratti:
Indirizzo: Vasella, A ETH Zentrum, Organ Chem Lab, Univ Str 16, CH-8092 Zurich, Switzerland ETH Zentrum Univ Str 16 Zurich Switzerland CH-8092 Switzerland
Citazione:
H. Gunji e A. Vasella, "Oligonucleosides with a nucleobase-including backbone - Part 2 - Synthesisand structure determination of adenosine-derived monomers", HELV CHIM A, 83(7), 2000, pp. 1331-1345

Abstract

The synthesis and structure determination of adenosine-derived monomeric building blocks for new oligonucleosides are described. Addition of Me,Si-acetylide to the aldehyde derived from the known partially protected adenosine 1 led to the epimeric propargylic alcohols 2 and 3, which were oxidised to the same ketone 4, while silylation and deprotection led to 7 and 9 (Scheme I). Introduction of an I substituent at C(8) of the propargylic silyl ethers 10 and 11 was not satisfactory. The protected adenosine 12 was, therefore, transformed in high yield into the 8-chloro derivative 13 by deprotonation and treatment with PhSO2Cl; the iodide 15 was obtained in a similar way (Scheme 2). The 8-Cl and the 8-I derivatives 13 and 15 were transformed into the propargylic alcohols 17 18, 25, and 26, respectively (Scheme 3). The propargylic derivatives 2, 10, 17 19, 23, 25, and 27 were correlated, andtheir (5'R) configuration was determined on the basis of NOEs of the anhydro nucleoside 19; similarly, correlation of 3, 11, 18, 20, 24, 26, and 28, and NOE's of 20 evidenced their (5'S)configuration.

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Documento generato il 30/11/20 alle ore 00:28:20