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Titre du document / Document title

A facilitated cyclic ether formation and its potential application in solid-phase peptide and organic synthesis

Auteur(s) / Author(s)

SHAN D. (1) ; ZHENG A. (1) ; BALLARD C. E. (1) ; WANG W. (1) ; BORCHARDT R. T. (2) ; WANG B. (1) ;

Affiliation(s) du ou des auteurs / Author(s) Affiliation(s)

(1) Department of Chemistry, North Carolina State University, Raleigh, NC, 27695-8204, ETATS-UNIS
(2) Department of Pharmaceutical Chemistry, The University of Kansas, Lawrence, KS 66047, ETATS-UNIS

Résumé / Abstract

A trimethyl lock system has been known to facilitate lactonization reactions through what has been termed a stereopopulation control mechanism. We have found that a similar trimethyl lock system can also facilitate cyclic ether formation with the concomitant release of a carboxylic acid in the presence of anhydrous tetrabutylammonium fluoride. To study this base-mediated trimethyl lock-facilitated cyclic ether formation, we synthesized fifteen model compounds. All model compounds underwent base-mediated cyclic ether formation in high yields at 0°C to room temperature (r.t.) with the concomitant release of the attached carboxylate. Such a system potentially could be used for the development of a two-dimensional linker for solid phase peptide and organic synthesis.

Revue / Journal Title

Chemical and pharmaceutical bulletin    ISSN  0009-2363   CODEN CPBTAL 

Source / Source

2000, vol. 48, no2, pp. 238-244 (12 ref.)

Langue / Language

Anglais

Editeur / Publisher

JAACC, Tokyo, JAPON  (1958) (Revue)

Mots-clés anglais / English Keywords

Chemical synthesis

;

Cyclization

;

Heterocyclization

;

Oxygen heterocycle

;

Chemical reduction

;

Quinone

;

Diphenols

;

Chroman derivatives

;

Decarboxylation

;

α-Aminoacid

;

Basic medium

;

Sodium Dithionites

;

Tetrahydrofurane

;

Organic solvent

;

Mots-clés français / French Keywords

Synthèse chimique

;

Cyclisation

;

Hétérocyclisation

;

Hétérocycle oxygène

;

Réduction chimique

;

Quinone

;

Diphénols

;

Chromane dérivé

;

Décarboxylation

;

α-Aminoacide

;

Milieu basique

;

Sodium Dithionite

;

THF

;

Solvant organique

;

α-Aminoacide ester 3-[2,5-dihydroxy-4,6-diméthylphényl]-3-méthylbutyle

;

1-Benzopyran-6-ol(2,3-dihydro-4,4,5,7-tétraméthyl)

;

1-Benzopyrane dérivé

;

Mots-clés espagnols / Spanish Keywords

Síntesis química

;

Ciclización

;

Heterociclización

;

Heterociclo oxígeno

;

Reducción química

;

Quinona

;

Difenoles

;

Descarboxilación

;

α-Aminoácido

;

Medio básico

;

Sodio Ditionito

;

Furano(tetrahidro)

;

Solvente orgánico

;

Localisation / Location

INIST-CNRS, Cote INIST : 4123, 35400008637788.0140

Nº notice refdoc (ud4) : 1309691



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