2-Deoxystreptamine
Structural Formula Vector Image
Title: 2-Deoxystreptamine
CAS Registry Number: 2037-48-1
Additional Names: 2-Deoxy-1,3-myo-inosadiamine; 1,3-diamino-4,5,6-trihydroxycyclohexane
Molecular Formula: C6H14N2O3
Molecular Weight: 162.19
Percent Composition: C 44.43%, H 8.70%, N 17.27%, O 29.59%
Literature References: Important component of several aminocyclitol antibiotics. Production by acid hydrolysis of neamine, q.v. and structure: F. A. Kuehl et al., J. Am. Chem. Soc. 73, 881 (1952). Also obtained from hydrolysis products of kanamycins, paromomycins, gentamicins, q.q.v. and other aminoglycoside antibiotics. See K. L. Rinehart, J. Infect. Dis. 119, 345 (1969); S. Hanessian, T. H. Haskell, The Carbohydrates vol. IIA, W. Pigman, D. Horton, Eds. (Academic Press, New York, 2nd ed., 1970) pp 159-172. Configuration: J. Daly et al., J. Am. Chem. Soc. 82, 5928 (1960); H. E. Carter et al., ibid. 83, 3723 (1961); R. U. Lemieux, R. J. Cushley, Can. J. Chem. 41, 858 (1963). Synthesis: M. Nakajima et al., Tetrahedron Lett. 1964, 967; T. Suami et al., ibid. 1967, 2671; S. Ogawa et al., J. Org. Chem. 39, 812 (1974); H. Prinzbach et al., Angew. Chem. Int. Ed. 14, 225 (1975); S. Ogawa et al., J. Org. Chem. 42, 3083 (1977). Review of syntheses: G. F. Busscher et al., Chem. Rev. 105, 775-791 (2005).
Properties: Colorless crystals from ethanol, mp 225-228°.
Melting point: mp 225-228°
 
Derivative Type: Dihydrochloride
CAS Registry Number: 14429-30-2
Molecular Formula: C6H14N2O3.2HCl
Molecular Weight: 235.11
Percent Composition: C 30.65%, H 6.86%, N 11.92%, O 20.42%, Cl 30.16%
Properties: Crystals, mp 325° (dec), H. Hitomi et al., Chem. Pharm. Bull. 9, 340 (1961).
Melting point: mp 325° (dec), H. Hitomi et al., Chem. Pharm. Bull. 9, 340 (1961)

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