GB1319303A - Sugar derivatives - Google Patents

Abstract

1319303 Mono- and di-alkylidenefuranosylamines UNIVERSITY OF BRADFORD 14 July 1971 [14 July 1970 3 Nov 1970] 34176/70 and 52219/70 Heading C2C Novel acid addition salts of mono- and dialkylidenefuranosylamines are prepared by reacting a pyranosylamine of Formula I (in which R 1 is H, CH 3 or CH 2 OH, R 2 is H, NH 2 or OH, R 3 is H or CH 2 OH and R 4 and R 5 are H, C 1-6 alkyl or aryl) and which is such that, in the furanose form, it possesses at least one pair of 1,2-cis or 1,3-cis hydroxyls, with a carbonyl compound of formula (in which each of R 6 and R 7 is H, C 1-6 alkyl or aryl or R 6 and R 7 , together with the carbonyl group, form an alicylic ketone, in the presence of sufficient strong acid, e.g. an acid of the formula HX (where X is halogen, sulphate or p-toluenesulphonate), to ensure that the amino group remains protonated. Examples of compounds which can be prepared by the above method have the formulae The novel acid addition salts are useful in the preparation of known nucleosides such as imidazole, pyrimidine and purine nucleosides which have antibiotic, antitumour and immunosuppressant activity. In examples, 3-(2<SP>1</SP>,3<SP>1</SP>-oisopropylidene - # - D - ribofuranosyl) - 5 - cyanouracil, 3 - (# - D - ribofuranosyl) - 5 - cyanouracil, di - isopropylidene - mannofuranosylcyanouracil, α - D - mannofuranosyl - 5 - cyanouracil, methyl 5 - amino - 1 - (2<SP>1</SP>3<SP>1</SP> - O - isopropylidene- # - D- ribofuranosyl)imidazole - 4 - carboxylate, inosine, 5 - cyano - 3 - methyl - 1 - (31,51 - O - isopropyldiene - # - D - xylofuranosyl) - uracil, 5 - cyano- 3 - methyl - 1 - # - D - xylofuranosyluracil, 2,3- O - isopropylidene - 5 - cyano - 3 - methyl - 1 - α- L - rhamnofuranosyluracil, 5 - cyano - 3 - methyl- 1 - α - L - rhamnofuranosyluracil, 5,6 - O - isopropylidene - 5 - cyano - 3 - methyl - 1 - # - D- glucofuranosyluracil, 5 - cyano - 3 - methyl - 1- # - D - glucofuranosyluracil and N - hippuroyl- 2,3 - O - isopropylidene - # - D - ribofuranosylamine are prepared.