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Titolo:
Synthesis of uronic acid-containing xylans found in wood and pulp
Autore:
Oscarson, S; Svahnberg, P;
Indirizzi:
Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden Univ Stockholm Stockholm Sweden S-10691 Chem, S-10691 Stockholm, Sweden
Titolo Testata:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
fascicolo: 8, , anno: 2001,
pagine: 873 - 879
SICI:
1472-7781(2001):8<873:SOUAXF>2.0.ZU;2-#
Fonte:
ISI
Lingua:
ENG
Soggetto:
KRAFT PULP; GLYCOSIDES; REACTIVITY; HYDROLYSIS; PROTECTION; CONVERSION; DONORS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
25
Recensione:
Indirizzi per estratti:
Indirizzo: Oscarson, S Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden Univ Stockholm Stockholm Sweden S-10691 91 Stockholm, Sweden
Citazione:
S. Oscarson e P. Svahnberg, "Synthesis of uronic acid-containing xylans found in wood and pulp", J CHEM S P1, (8), 2001, pp. 873-879

Abstract

Two uronic acid-containing trisaccharides, (4-deoxy-beta -L-threo-hex-4-enopyranosyluronic acid)- and (4-O-methyl-alpha -D-gluropyranosyluronic acid)-(1 -->2)-beta -D-xylopyranosyl-(1 -->4)-D-xylopyranose, found in enzyme hydrolysates from pulp are synthesised. A common dixyloside 2'-OH acceptor, p-methoxyphenyl [3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-beta -D-xylopyranosyl]-(1 -->4)-2,3-di-O-benzoyl-beta -D-xylopyranoside, is constructed and coupled with two glucuronate thioglycoside donors differently substituted inthe 4-position, O-methyl and O-mesyl, respectively, to give trisaccharides. DMTST as promoter in diethyl ether gives exclusively the alpha -linked products in high yield. Treatment of the 4"-O-mesyl trisaccharide with DBU then gives the alpha,beta -unsaturated uronic acid derivative. The protectionpattern introduced in the acceptor allows continued synthesis of larger oligosaccharides. Removal of the butanedione acetal produces 3',4'-acceptors,and the p-methoxyphenyl glycoside can be transformed into various glycosyldonors, e.g. thioglycosides and sugar halides. Complete deprotection givesthe two target reducing trisaccharides.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 02/04/20 alle ore 00:19:03