121467-82-1Relevant articles and documents
Aminoglycoside Antibiotics - Enantiomerically Pure Sannamine Building Blocks
Kuehlmeyer, Rainer,Seitz, Bernhard,Weller, Thomas,Fritz, Hans,Schwesinger, Reinhard,Prinzbach, Horst
, p. 1729 - 1744 (2007/10/02)
Starting from the prochiral dianhydrodeoxy-epi-inositol 9 a highly efficient synthesis for rac-sannamines (1, salts, derivatives) and rac-de-O-methylsannamine (18, salt) has been developed.Key steps are two regiospecific, practically quantitative epoxide opening reactions: intramolecularly in the diepoxyurethanes 11 and intermolecularly in the epoxyurethanes rac-13.With (R)-1-phenylethylamine as potential primary amino group in the second step separation of the corresponding diastereomers (16, 16') is achieved without significant loss of material.By this route enantiomerically pure (de-O-methyl)sannamines become available in which all functionalities are protected except that to be glycosidated.Attempts for an asymmetric realization of this synthesis resulted in only very small ee(de) values. - Key Words: Antibiotics, aminoglycoside/ Sannamine building blocks/ Aminoglycosides