Process for the production of perbenzylated 1-O-glycosides

Details Process for the production of perbenzylated 1-O-glycosides Process for the production of perbenzylated 1-O-glycosides

2005-06-21

2005-06-21

Peselev, Elli (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

C536S004100, C536S017400, C536S116000, C536S120000

Reexamination Certificate

active

06908989

ABSTRACT:
The invention relates to a process for the production of perbenzylated 1-O-glycosides of general formula I or salts thereofin whichsugar1is a monosaccharide that is functionalized in 1-OH-position,R represents benzyl,n means 2, 3 or 4,X means —COO— or —NH—andL means a straight-chain, branched, saturated or unsaturated C1-C30carbon chain, which optionally is interrupted or substituted by groups.The process according to the invention starts from economical starting materials, provides good yields and allows the production of perbenzylated saccharides with 1-O-functionalized side chains on an industrial scale.

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Schmidt et al., “Neue Methoden zur Glycosid- und Oligosaccharidsynthese—gibt es Alternativen zur Koenigs-Knorr-Methode?” Angewandte Chemie, VCH Verlagsgesellschaft, Weinheim, DE, Bd. 98, 1986, Seiten 213-236.
Sugawara et al., “Synthesis of ω-(methoxycarbonyl)alkyl and 9-(methoxycarbonyl)-3,6-dioxanonyl glycopyranosides for the preparation of carbohydrate-protein conjugates,” Carbohydrate Research, Elsevier Scientific Publishing Company, Bd. 230, Nr. 1, 1992 Seiten 117-150.
Schmidt et al., “1-O-Alkylation of D-Glucopyranose,” Journal of Carbohydrate Chemistry, Bd. 3, Nr. 1, 1984, Seiten 67-84.
O. Lockhoff, “An Access to Glycoconjugate Libraries through Multicomponent Reactions,” Angewandte Chemie International Edition, Bd. 37, Nr 24, 1998, Seiten 3436-3439.

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