94592-14-0

Upstream product

• 94592-12-8 DL-(1α,2α,3β,4β,5α)-1,2-anhydro-3-O,4-N-carbonyl-4-(methylamino)-1,2,3,5-cyclohexanetetrol 
• 94592-11-7 (1α,2α,3β,4α,5α)-1,2:4,5-dianhydro-3-O-(methylcarbamoyl)-1,2,3,4,5-cyclohexane-pentol 
• 55990-89-1 (1α,2α,3β,4α,5α)-1,2:4,5-dianhydro-1,2,3,4,5-cyclohexane-pentol 
• 100-44-7 benzyl chloride 

Downstream Products

• 121467-80-9 DL-(1α,2β,3β,4α,6β)-6-azido-4-O-benzyl-3-O,4-N-carbonyl-3-(methylamino)-1,2,4-cyclohexanetriol 
• 121521-09-3 (+)-(1R)-(1α,2β,3β,4α,6β)-4-O-benzyl-2-O,3-N-carbonyl-3-(methylamino)-6-<(R)-(1-phenylethyl)amino>-1,2,4-cyclohexanetriol 
• 121521-10-6 (+)-(1S)-(1α,2β,3β,4α,6β)-4-O-benzyl-2-O,3-N-carbonyl-3-(methylamino)-6-<(R)-(1-phenylethyl)amino>-1,2,4-cyclohexanetriol 

Relevant academic research and scientific papers

Aminoglycoside Antibiotics - Enantiomerically Pure Sannamine Building Blocks

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