19 オリゴ糖をKey出発物質とする生理活性物質の合成 : マルトースから新アミノ配糖体の合成(口頭発表の部)

抄録

A resemblance of the molecular shapes between 1,4-diamino-cyclitol aminoglycoside antibiotics such as fortimicin A (1) and 1,6-anhydromaltose (2) prompted us to synthesize a new potential antimicrobial compound with structure analogous to the antibiotics, employing 2 as the starting material. The present paper describes the synthesis of a new 1,4-diaminocyclitol aminoglycoside (3), developing several novel synthetic methodology. The structural characteristic of 3, the absence of an equatorial methoxy group at C-4, regularly present in the natural antibiotics of this kind, resulted in no conformational inversion of the cyclitol moiety into the undesirable one. The following new processes were the particularly novel ones: (i) conversion of 1,6-anhydro-disaccharide to the corresponding phenyl thioglycoside by selective ring fission, (ii) the first application of Ferrier reaction to the thioglycoside for its transformation to a cyclohexanone derivative, and (iii) selective hydrogenation of a C-C double bond without reducing the coexisting azido groups.