PREPARATION OF GARAMINE AND TRI-N-SUBSTITUTED GARAMINE AND INTERMEDIATES PRODUCED THEREBY

摘要

1473178 Garamine and its derivatives SCHERICO Ltd 24 June 1974 [26 June 1973] 27957/74 Heading C2C Garamine or its N-protected derivatives are prepared by treating an N-protected pseudotrisaccharide in which a garamine moiety is glycosidically linked to another pyranoside sugar which possesses vicinal hydroxy groups with a glycol cleaving agent reducing the secodialdehyde derivative formed with a metal borohydride to form a seco-dihydroxy derivative which is treated with dilute aqueous acid (optionally after replacing the amino-protecting groups with other amino-protecting groups) to form an N-protected garamine from which the protecting groups may be removed. Novel intermediate compounds IV in which R 1 is H or Me, R 2 is OH or NHR, Z is CH 2 OH or -CH(NHR)-CH 2 OH and R is hydrogen or an amino protecting group are prepared by utilizing the above process to form compounds IV (R = amino-protecting group) and if desired deprotecting the amino groups to form compounds IV (R=H). The amino-protecting groups used are benzyloxycarbonyl, methoxycarbonyl, ethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, acetyl, propionyl, caproyl or benzoyl. N-protected derivatives of Gentamicin B, B 1 and X 2 and mixtures thereof, of Antibiotic J20A and J20B and mixtures thereof and of Antibiotic G-418 are prepared.