121394-00-1

Basic information

• Product Name: (1α,2α,3β,4α,5α)-1,2:4,5-dianhydro-3-O-<(R)-(1-phenylethyl)carbamoyl>-1,2,3,4,5-cyclohexanepentol
• CAS NO: 121394-00-1
• Molecular Weight: 275.304
• Mol File: 121394-00-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1α,2α,3β,4α,5α)-1,2:4,5-dianhydro-3-O-<(R)-(1-phenylethyl)carbamoyl>-1,2,3,4,5-cyclohexanepentol(CAS DataBase Reference)
• NIST Chemistry Reference: (1α,2α,3β,4α,5α)-1,2:4,5-dianhydro-3-O-<(R)-(1-phenylethyl)carbamoyl>-1,2,3,4,5-cyclohexanepentol(121394-00-1)
• EPA Substance Registry System: (1α,2α,3β,4α,5α)-1,2:4,5-dianhydro-3-O-<(R)-(1-phenylethyl)carbamoyl>-1,2,3,4,5-cyclohexanepentol(121394-00-1)

Safety Data

• Hazardous Substances Data: 121394-00-1(Hazardous Substances Data)

Upstream product

• 55990-89-1 (1α,2α,3β,4α,5α)-1,2:4,5-dianhydro-1,2,3,4,5-cyclohexane-pentol 
• 33375-06-3 (1R)-1-phenylethyl isocyanate 

Downstream Products

• 121394-02-3 (1R)-(1α,2α,3β,4β,5α)-1,2-anhydro-3-O,4-N-carbonyl-4-<(R)-(1-phenylethyl)amino>-1,2,3,5-cyclohexanetetrol 
• 121394-03-4 (1S)-(1α,2α,3β,4β,5α)-1,2-anhydro-3-O,4-N-carbonyl-4-<(R)-(1-phenylethyl)amino>-1,2,3,5-cyclohexanetetrol 

Relevant articles and documents

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