CS276698B6 - 1,2: 3,4-di-0-isopropylidene-6-0-epoxypropyl-I-D-galactopyranose - Google Patents

Abstract

The new 6-O-epoxypropyl derivative of diisopropylidene-D-galactose of formula I is used as an intermediate, for example, in the production of water-soluble drugs and disinfectants.

Description

Field of technology

The invention relates to a novel 6-O-epoxypropyl derivative of diisopropylidene-D-galactose.

Prior art

Some biologically active substances, such as drugs and disinfectants, are insoluble or sparingly soluble in water. This problem is solved by adding surfactants to the mixture or by forming a hydrophilic group in the molecule. This improves the possibility of their application. For example, quaternary ammonium salts have been obtained from sulfanilamides (Boll. Chini. Farm., 122, 1983, M. Ferappi, A. Carotti, G. Casini, Quantitative Structure Activity Relationship of Some Antibacterial Quaternary Ammonium Salts Derivatives from Sulfanilamide, pp. 73 to 78). Hydrochlorides and quaternary ammonium salts have been prepared from betaine esters (Physiol. Akt. Veshchestva, £ 4, 1982, A. Kovalenko, ER Alieva, IG Khaskin, Effect of Betaine Hydrochloride Esters on Microflora in Alcohol Production from Molasses, p. 86 to 91). A mixture of 2-benzyl-4-chlorophenol, alkylnaphthalenesulfonates, sulfobetaines and acrylic polymers had bactericidal effects (U.S. Pat. No. 4,257,907). Heterocyclic amines oxidized to anine oxides also have good antimicrobial effects (Folia Microbiol., 23, 1978, D. Mlynarčík, V. Čupková, F. Devínsky, I. Lacko, Antimicrobial Efficiency of Saturated Heterocyclic Amine Oxides, pp. 493-495). The attachment of a hydrophilic group can have undesirable side effects on a living organism. Therefore, it was important to find a hydrophilic group that does not have these side effects. 1,2: 3,4-Di-O-isopropylidene-6-O-epoxypropyl-D-galactopyranose has not yet been published and has been prepared by us according to a known procedure (Synthesis, 1983, G. Mouzin, H. Cousse, JP Rieu, A. Duflos, A Convenient One-Step Synthesis of Glycidyl Ethers, pp. 117-119).

The essence of the invention

The invention relates to 1,2: 3,4-di-O-isopropylidene-6-O-epoxypropyl-D-galactopyranose of the formula I

/ 1 / 1,2: 3,4-Di-O-isopropylidene-6-O-epoxypropyl-2-D-galactopyranose contains a reactive epoxide group which can be attached to biologically active compounds. Subsequent removal of the isopropylidene protecting groups gives a hydrophilic portion of the compound. The compound thus treated has no undesirable side properties.

Examples of embodiments of the invention

Example 1

To 13.3 ml of 50 wt. % aqueous sodium hydroxide solution is added with stirring 8.3 ml of chloromethyloxirane and 0.28 g of tetrabutylammonium hydrogen sulphate. After cooling to 20 DEG C., 5.2 g (0.02 mol) of 1,2: 3,4-di-O-isopropylidene-d.-D-galacto are added over 30 minutes.

CS 276698 86 2 pyranoses. The reaction mixture was cooled in such a way that the temperature did not rise above 28 ° C. The reaction is complete after 4 hours. The mixture was poured into ice water (50 nil). After separation, the aqueous phase is extracted three times with ether (200 ml each). The ether extract was combined with the oily layer and washed with saturated aqueous sodium chloride solution until the extract was neutral. The ether solution was dried over anhydrous sodium sulfate, and the ether was distilled off. The distillation residue is separated on a neutral alumina column, the elution mixture is ethyl acetate and hexane in a volume ratio of 1: 1. The purified product is crystallized from ether. The 1,2: 3,4-di-O-isopropylidene-6-O-epoxypropyl-c2-D-galactopyranose obtained is a white crystalline substance with a melting point of 68-70 ° C. The reaction yield was 74.4%. In the infrared spectrum, the following determining absorption bands are: 3056, 2987, 2871, 1381, 1258, 1175, 1157, 1139, 1119, 915 and 906 cm ^-1 . In the mass spectrum, the following determining peaks are: 301, 243, 229, 171, 134, 124, 100, 85 and 82. Elemental analysis for C 11 H 21 N 2 O, molecular weight 316.35 calculated: 56.96 wt. % carbon, 7.65 wt. % hydrogen detected; 56.86 wt. % carbon, 7.70 wt. % hydrogen.

Claims (1)

Industrial use 1,2: 3,4-Di-O-isopropylidene-6-O-epoxypropyl-N-galactopyranose is used as an intermediate, for example, in the manufacture of water-soluble drugs and disinfectants. 1,2: 3,4-Di-O-isopropylidene-6-O-epoxypropyl-6-D-galactopyranose of formula I CH 2 -O-CH-CH-CH 2 O 3 / 1 /