PROCESS FOR PRODUCING 2'-O-FUCOSYLLACTOSE

• Main Authors: PUHL, Michael, WOELFERT, Andreas, SIEGEL, Wolfgang, RENZ, Stephanie
• Format: Patent
• Language: English; French; German
• Published: 12.12.2018
• Subjects: CHEMISTRY; DAIRY PRODUCTS, e.g. MILK, BUTTER, CHEESE; DERIVATIVES THEREOF; FOODS OR FOODSTUFFS; FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BYSUBCLASSES A23B - A23J; HUMAN NECESSITIES; MAKING THEREOF; METALLURGY; MILK OR CHEESE SUBSTITUTES; NUCLEIC ACIDS; NUCLEOSIDES; NUCLEOTIDES; ORGANIC CHEMISTRY; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL; SUGARS; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OFNUTRITIVE QUALITIES, PHYSICAL TREATMENT; THEIR TREATMENT, NOT COVERED BY OTHER CLASSES

The present invention relates to a process for producing 2'-O-fucosyllactose, to the intermediates obtainable by this process and to the use of these intermediates. Production comprises the reaction of a protected fucose of general formula (I) with a tri-(C1-C6-alkyl)silyl iodide to form a protected 1-iodofucose followed by reaction of the protected 1-iodofucose with a compound of general formula (I I), in the presence of at least one base and deprotection of the obtained coupling product to obtain 2'-O-fucosyllactose. The variables are defined as follows: Raand Rb are identical or different and represent -C(=O)-C1-C6-alkyl or -C(=O)-phenyl, wherein phenyl is unsubstituted or optionally comprises 1 to 5 substituents or Ra and Rb together represent a -(C=O)- radical or a substituted methylene radical -C(RdRe)-, Rc represents an RSi radical or benzyl, wherein benzyl is unsubstituted or optionally bears 1, 2 or 3 substituents, RSi represents a radical of formula SiRfRgRh, wherein Rf, Rgand Rh are identical or different and represent, for example C1-C8-alkyl, R1 represents a -C(=O)-R11 radical or a SiR12R13R14 radical, R2 are identical or different and represent for example C1-C8-alkyl, R3 are identical or different and represent for example C1-C8-alkyl or both radicals R3 together represent linear C1-C4-alkenyl which is unsubstituted or bears 1 to 6 methyl groups as substituents.