C - Chemistry – Metallurgy – 07 – H
Patent
C - Chemistry, Metallurgy
07
H
C07H 15/18 (2006.01) A61K 31/7016 (2006.01) A61K 31/702 (2006.01) C07D 493/04 (2006.01) C07H 1/00 (2006.01) C07H 3/04 (2006.01) C07H 5/04 (2006.01) C07H 13/12 (2006.01) C07H 15/08 (2006.01) C07H 15/12 (2006.01) C07H 15/14 (2006.01) C07H 15/26 (2006.01) C07H 17/04 (2006.01) C07H 23/00 (2006.01)
Patent
CA 2396966
This invention relates to reagents and methods for synthesis of biologically active di- and tri-saccharides comprising .alpha.-D-Gal(1.fwdarw.3)-D-Gal. In particular the invention provides novel reagents, intermediates and processes for the solution or solid phase synthesis of .alpha.-D-galactopyranosyl- (1.fwdarw.3)-D-galactose, and derivatives thereof. In one preferred embodiments the invention provides a protected monosaccharide building block of general formula (II): in which R3 is methoxy or methyl; R1 is H, benzoyl, pivaloyl, , 4-chlorobenzoyl, acetyl, chloroacetyl, levulinoyl, 4- methylbenzoyl, benzyl, 3,4-methylenedioxybenzyl, 4-methoxybenzyl, 4- chlorobenzyl, 4-acetamidobenzyl, or 4-azidobenzyl; and R2 is H, Fmoc, benzoyl, pivaloyl, 4-chlorobenzoyl, acetyl, chloroacetyl, levulinoyl, 4-methylbenzoyl, benzyl, 3,4-methylenedioxybenzyl, 4-methoxybenzyl, 4-chlorobenzyl, 4- acetamidobenzyl, or 4-azidobenzyl.
La présente invention concerne des réactifs et des procédés de synthèse de di- et trisaccharides biologiquement actifs contenant .alpha.-D-Gal(1.fwdarw.3)-D-Gal. Plus particulièrement, cette invention concerne de nouveaux réactifs, intermédiaires et procédés de synthèse en phase solution ou en phase solide de .alpha.-D-Galactopyranosyl-(1.fwdarw.3)-D-Galactose, et leurs dérivés. Dans un mode préféré de réalisation, l'invention décrit un motif structural de monosaccharide protégé représenté par la formule générale (II): dans laquelle R?3¿ représente méthoxy ou méthyle; R?1¿ représente H, benzoyle, pivaloyle, 4-chlorobenzoyle, acétyle, chloroacétyle, levulinoyle, 4-méthylbenzoyle, benzyle, 3,4-méthylènedioxybenzyle, 4-méthoxybenzyle, 4-chlorobenzyle, 4-acétamidobenzyle, or 4-azidobenzyle; et R?2¿ représente H, Fmoc, benzoyle, pivaloyle, 4-chlorobenzoyle, acétyle, chloroacétyle, levulinoyle, 4-méthylbenzoyle, benzyle, 3,4-méthylènedioxybenzyle, 4-méthoxybenzyle, 4-chlorobenzyle, 4-acétamidobenzyle, ou 4-azidobenzyle.
Bornaghi Laurent
Dekany Gyula
Drinnan Nicholas Barry
Papageorgiou John
West Michael Leo
Alchemia Pty. Ltd.
Ridout & Maybee Llp
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