METHOD FOR PREPARATION OF α-GALACTOSYL CERAMIDE COMPOUNDS Russian patent published in 2018 - IPC C07H15/04 C07H15/18 

FIELD: chemistry.

SUBSTANCE: present invention relates to a process for the preparation of compounds of formula (I) . Method comprises step a) glycosylating a compound of formula (II) with a compound of formula (III) to obtain a compound of formula (IV) (IV), step b) deprotection to obtain a compound of formula (V) (V) or formula (VI) (VI), step c) coupling the compound of formula (V) or (VI) with a compound of formula R₂COCl (VII) in the presence of a base and step d) deprotection to obtain a compound of formula (I); and the process comprises two steps of purification by column chromatography on silica gel, where R₁ is C₁-C₂₀-alkyl; R₂ is C₁-C₃₀-alkyl; R₃ is C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-acyl or benzoyl; R₄ is H or C₁-C₆-alkyl; or R₃ and R₄ together with the nitrogen atom to which they are attached form C₂-C₆-heterocycloalkyl or C₁-C₅-heteroaryl; PG₁ is an acetyl, benzyl, benzoyl, methoxyethoxymethyl ether, dimethoxytrityl, methoxymethyl ether, methoxytrityl, p-methoxybenzyl ether, methylthiomethyl ether, pivaloyl, tetrahydropyranyl, trityl and silyl ethers, trimethylsilyl, tert-butyldimethylsilyl, triisopropylsilyloxymethyl and triisopropylsilyl; PG₂ is selected from carboxybenzyl, p-methoxybenzylcarbonyl, tert-butyloxycarbonyl, 9-fluorenylmethyloxycarbonyl, acetyl, benzoyl, benzyl, carbamate groups, p-methoxybenzyl, 3,4-dimethoxybenzyl, p-methoxyphenyl, tosyl and other sulfonamide groups; PG₃ and PG'₃ are selected from acetyl, benzyl, benzoyl, methoxyethoxymethyl ether, dimethoxytrityl, methoxymethyl ether, methoxytrityl, p-methoxybenzyl ether, methylthiomethyl ether, pivaloyl, tetrahydropyranyl, trityl and silyl ethers, trimethylsilyl, tert-butyldimethylsilyl, triisopropylsilyloxymethyl and triisopropylsilyl; LG is selected from triflate, tosylate and mesylate, halides, nitrates, phosphates and imidates.

EFFECT: present invention can be used in the chemical industry.

10 cl, 7 ex