CS225600B1 - Beta-laktozylmethylamine,beta-maltosylmethylamine,beta-cellobiosylmethylamine and their preparation - Google Patents

Description

CZECHOSLOVENSKASOC 1 AND LI ST 1 C CAMPAIGN (19) DESCRIPTION FIXED TO COPYRIGHT CERTIFICATE 225600 (11) (Bl) 'í i (51) Int Cl.3 (23) Exhibition Priority C 07 H 5/06 (22) Registered 05 11 82 (21) PV 7895-82 bW (40) Published 24 06 83 OFFICE AND DISCOVERY OFFICE (45) Issued 30 09 85 (75).

Author of the invention PETRUS LADISLAV ing. CSc., BILIK VOJTECH RNDr. DrSc., BRATISLAVA (54) 1-Lactosylmethylamine, 10-maltosylinethylamine, S-celobiosylmethylamine for their preparation

The present invention relates to β-lactosylmethylamine, β-maltosylmethylamine, β-cellobiosylmethylamine and to a process for their preparation.

Glycosylmethylamines as derivatives of saccharides suitable for glycosylation of proteins are known only as monosaccharide derivatives. They are prepared by catalytic reduction of glycosylnitromethanes with gaseous hydrogen by nanofiber [J. C. Sowden and M. L. Oftedahl: J. Org. Chem. 26, 1974 (1961); L. Houhg and S.H. Shute: J. Chem. Soc. 4633 (1962)) aleboplatin catalyst [J. C. Sowden, C. H.Bowers and K. O. Lloyd: J. Org. Chem., 29, 130 (1964); S. W. Gunner, R. D. King, W. G. Ove-rend, and N. R. Williams: J. Chem. Soc. (C) 1954 (1970)]. The efficient process by which β-D-glucopyranosylmethylamine and β-D-galactopyranosylmethylamine have been prepared is the reduction of the glycosylnitromethanes by the action of ferrous hydroxide [L. Petrus, MS. copyright certificate No.225315],

The proposed method extends the range of glycosylmethylamines to three disaccharide derivatives. SUMMARY OF THE INVENTION The present invention provides β-lactosylmethylamine, β-maltosylmethylamine and β-cellobiosylmethylamine of the formula R —CH 2 -NH 2 wherein R is β-lactosyl, β-maltosyl or β-celobiosyl. The present invention further provides a process for the preparation of a compound of the general formula R-CH 2 -NH 2, characterized in that the starting 3-lactosylnitromethane, 3-maltosylnitromethane or β-cellobiosylnitromethane of the formula R-CH 2 —NO 2 is reduced in aqueous ferrous sulfate solution ammonia at 90 to 100 ° C and pH> 8 for 5 to 20 minutes. The advantage of the proposed process for the preparation of the disaccharide glycosylmethylamines is that it allows for simple isolation of the product. The process is simple and easy to use chemicals and equipment. The starting disaccharide glycosyl nitro methanes are available substances and produce the corresponding carbon-reducing disaccharide nitromethane synthesis and subsequent dehydration of the intermediate [L. Petruš, S. Bystrický, T. Sticzay and V. Bílik: Chem. Rumors 36, 103 (1982)]. Example 1

To a boiling solution of ferrous sulfate heptahydrate (10.1 g) in water (24 mL) was added a solution of β-lactosylnitromethane (2 g) in water (10 mL). Then, concentrated aqueous ammonia solution (3 ml) was added portionwise immediately after intensive stirring until the boiling solution was significant (pH > 8). Finally, the reaction mixture was boiled for 10 min (the required alkali was still maintained by addition of ammonium). The precipitate was filtered off and washed with 2% aqueous ammonia solution (50 mL). Anion exchange in hyd 225600 was added to the cooled filtrate.

Claims (2)

Approximately half the liquid volume was distilled off from the suspension on a rotary evaporator under reduced pressure (about 5 kPa). The anion was filtered off and washed (3 X 50 mL). Concentration of the filtrate yielded pure β-lactosylmethylamine (1.3 g; 70%) which, after dissolution in methanol, crystallized after several days on vessel flasks such as β-lactosylmethylamine carbonate by 1.139-140 ° C and laI □ + 19 ° (water, c 2). For C13H25NOh. H 2 CO 3 calculated C 40.28; H, 6.52; 3.36% N; H, 6.72; N, 3.46%. EXAMPLE 2 By the same procedure as in Example 1, 3-maltosylnitromethane (2 g) was obtained by concentrating the final filtrate (rotary evaporator, 5 kPa). 40 ° C, 5h) 3-Maltosylmethylamine hydrate (1.2g, 63%) as an amorphous hygroscopic substance with a / a / g * + 93 ° (water, c 2). For C 13 H 25 NO 10. H, 7.29; N, 3.75. Found: C, 42.04; H, 7.43; N, 3.50. EXAMPLE 3 Z-Cellobiosylnitromethane (1 g) Example 2 gave O-cellobiosylmethylamine hydrate (0.7 g, 73%) as an amorphous hygroscopic material with a pH of + 2 ° (water, c 2). For C13H25NO10 H2O, C, 42.17; H, 7.39; N, 3.53. OBJECT What is claimed is: 1. Compounds of [2-lactosylmethylamine, [beta] -malozylmethylamine and (S-celobiosylmethylaminone of the general formula R-CH2-NH2, wherein R is S-lactosyl, N-maltosyl or [beta] -celobiosyl). 2. Process for the preparation of the compounds of the general formula R-CH2-NH2 according to item 1, wherein R is as defined in point 1, characterized in that the starting .beta.-lactosyl nitromethane, .beta.-maltosylnitromethane or .beta.-cellobiosylnitromethane of the general formula R-CH 2 -NO 2 is reduced in an aqueous solution of ferrous sulfate and ammoniacal at 90-100 ° C and pH> 8 for 5-20 minutes. T 54 1640-65