CZ242091A3 - di-beta-l-ramnopyranosylamine and process for preparing thereof - Google Patents

Abstract

A compound of a formula I, wherein R is hydrogen or acyl group, can be prepared from beta-L-rhamnopyranosylamine by action of anhydrous methanol at a temperature of from 50 to 64 degrees of Celsius for 1 to 5 hours. The compound of the formula I, wherein R is acetyl group, is prepared by O-acetylation of the originated product of the previous reaction in an acetic anhydride and pyridine medium at a temperature of from 15 to 25 degrees of Celsius for 16 to 32 hours. Quoted compounds can be used in an organic chemistry and biochemistry branch at inhibition of L-rhamnosidases.

Description

Technical field

The present invention relates to a di-beta-L-rhamnopyranosylamine of formula I

(I) wherein R is hydrogen or a process for its preparation.

acyl group,

The prior art

The compounds of formula I have not been described in the literature. By their structure, they can be classified into a group of substances that inhibit the activity of certain enzymes (P.Lalgerie, G.Legler, JMYon: Biochemistry, 64, 977 (1982); K.Linek, J.Alf.Bldi, J.Defaye: Carbohydr. Res., 164, 195 (1987)].

SUMMARY OF THE INVENTION

SUMMARY OF THE INVENTION The present invention is based on the fact that the new compounds - di-beta-L-rhamnopyranosylamine of the formula I

wherein R is hydrogen or acyl

The principle of the process for the preparation of the di-beta-L-rhamnopyranosylamine of the formula I in which R is hydrogen consists in that on the beta-L-rhamnopyranosylamine of the formula II

NH, (II) is treated with anhydrous methanol at 50 to 64 ° C for 1 to 5 hours.

A process for the preparation of a di-beta-L-rhamnopyranosylamine of the formula I in which R is acyl is to impregnate the beta-L-rhamnopyranosylamine of the formula II with anhydrous methanol at a temperature of 50 to 64 ° 0 for 1 to 5 hours and the reaction product is acetylated in acetic anhydride and pyridine at 15-25 ° C for 16-32 hours.

The starting beta-L-rhamnopyranosylamine is prepared according to methods known in the literature (H.S.Isbell, H. L. Frush: Methods Garbohydr. Chem., 8, 255 (1980)). The final product is obtained by transglycosylation or dimerization; its structure, anomeric configuration and troscopy.

conformations were determined by H- and ^J -nmr spectra

Example 1

Preparation of di-be-L-rhamnopyranozylamine

Beta-L-rhamnopyranosylamine (10 g, 0.061 mol) in anhydrous methanol (500 mL) was refluxed for 1 h, excluding air humidity. By concentrating the solution, di-beta-L-rhamnopyranosylarine started to crystallize - crystallization was complete at 0 ° C within 24 hours. The resulting crystalline material was filtered off and dried over £ 55. The yield of the reaction was 9 g, ie 47.5%. The di-beta-L-rhamnopyranosylamine thus prepared was recrystallized from ethanol-acetone. Mp 110 ° C, [α] ²⁵ D + 52.0 ° (c 2.0, H ₂ O).

Example 2

Preparation of bis (2,3,4-tri-O-acetyl-beta-L-rhamnopyranosyl) amine

The di-beta-L-rhamnopyranosylamine from Example 1 (9 g, 0.029 mol) was acetylated with a mixture of acetic anhydride (45 mL, 0.48 mol) and pyridine (90 mL). The solution was stirred at 20 ° C for 24 h. The reaction mixture was poured into ice water (500 mL) to give a crystalline substance which was filtered off and dried over θ2 ° C. 7% o Bis (2,3,4-tri-O-acetyl-beta-L-rhamnopyranosyl) amine thus prepared had a m.p.

130 ° C and + 23 ° (c 2.0, chloroform).

Industrial applicability

The invention can be used in organic chemistry. It can also find utility in biochemistry as an inhibitor of L-rhamnididases.

Claims (3)

PATENTOVÉ - 4 N Di-beta-L-rhamnopyranosylamine YEARS -a ί> O I o <c · The salt of formula (I) 2. A process for the preparation of a di-beta-L-rhamnopyranosylamine of the formula I according to claim 1, wherein R is hydrogen, characterized in that the beta-L-rhamnopyranosylamine of the formula III is treated with anhydrous methanol at 50-64 ° C for 1 to 5 hours · 3. A process for the preparation of a di-beta-L-rhamnopyranosylamine of the formula I according to claim 1, wherein R is acyl, characterized in that the beta-L-rhamnopyranosylamine of the formula III is treated with anhydrous methanol at 50 to 64 ° C for For 1 to 5 h, the resulting reaction product is O-acetylated in acetic anhydride and pyridine at 15-25 ° C for 16-32 hours. Eί, 'Κ' - ^e:> 1 Η Η