Protecting groups useful in the synthesis of...

C - Chemistry – Metallurgy – 07 – H

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C07H 15/18 (2006.01)

Patent

CA 2391966

One aspect of the present invention relates to optionally substituted halogenated benzyl halides and the like. These compounds are useful as halogenated benzyl ether-based protecting groups for a variety of functional groups. Another aspect of the present invention relates to use of said protecting groups in an orthogonal protecting group strategy for the synthesis of complex molecules that comprise a number of suitable functional groups. Another aspect of the present invention relates to saccharides bearing various arrays of protecting groups of the present invention. Another aspect of the present invention relates to a method of synthesizing an oligosaccharide or glycoconjugate, comprising the steps of: using a saccharide bearing at least one protecting group of the present invention to glycosylate a second molecule to give a product comprising said saccharide; and removing a protecting group of the present invention from said product.

La présente invention concerne, d'une part, des halogénures de benzyle halogéné éventuellement substitués et d'autres composés semblables. Ces composés sont utilisés comme groupes protecteurs à base d'éther de benzyle halogéné pour divers groupes fonctionnels. L'invention concerne, d'autre part, l'utilisation de ces groupes protecteurs dans une stratégie de groupe protecteur orthogonal pour la synthèse de molécules complexes comprenant un certain nombre de groupes fonctionnels appropriés. La présente invention concerne également des saccharides portant divers réseaux de groupes protecteurs de l'invention. L'invention concerne en outre une méthode de synthèse d'un oligosaccharide ou glycoconjugué, consistant à utiliser un saccharide portant au moins un groupe protecteur de la présente invention pour glycosyler une seconde molécule afin d'obtenir un produit comprenant ledit saccharide, et à éliminer dudit produit un groupe protecteur de la présente invention.

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