Gem difluorinated c-glycopeptides, their preparation and their use for the preservation of biological materials and/or in cryosugery

Abstract

The invention concerns a gem-difluorinated C-glycopeptide compound of formula (I) in which N is an integer between 1 and 5, R=H, AA, AA-AAand R=OH, AA, AA, AA, with AA, and AAare independents groups and represent amino acids with a non-functionalized side chain and R, R, Rare independent groups and one of them is equal to formula (II), in which n is an integer between 3 and 4, Y, Y' are independent groups in which Y, Y′=H, OR, N, NR′R″, SR″′, where R=H, benzyl, trimethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl, acetate group, R′, R″′═H, alkyl, allyl, benzyl, tosylate group, C(═O)-alkyl, C(═O)−Bn, R″′=H, alkyl, acetate group, Ris notably a group H, CH, CHOH, CH-Glycoside group, CH-OGP in which GP is a protector group such as an alkyl, benzyl, trimethylsilyl, tert-butyldimethylsilyl, tertbutyldiphenylsilyl, acetate group,; and R=OH, OGP′, NH, N, NHGP′, NGP′GP″ in which GP′ and GP″ is or not a protector group such as an alkyl, benzyl, trimethylsilyl, tertbutyldimethylsilyl, tert-butyldiphenylsilyl, acetate group, and Ris a hydrogen atom H or a free or protected alcohol function. It applies notably to preservation of biological materials and to cryosurgery.