Title: Desosamine
CAS Registry Number: 5779-39-5
CAS Name: 3,4,6-Trideoxy-3-(dimethylamino)-D-xylo-hexose
Additional Names: 4-dimethylaminotetrahydro-6-methylpyran-2,3-diol; picrocine
Molecular Formula: C8H17NO3
Molecular Weight: 175.23
Percent Composition: C 54.83%, H 9.78%, N 7.99%, O 27.39%
Literature References: Sugar component of several macrolide antibiotics, such as the erythromycins. Isoln: Clark, Antibiot. Chemother. 3, 663 (1953). Identity with picrocine: Brockmann et al., Ber. 87, 856 (1954). Stereochemistry: Woo et al., Tetrahedron Lett. 1962, 735. Configuration: Bolton et al., Chem. Ind. (London) 1962, 1945; Foster et al., J. Chem. Soc. 1965, 2318. Synthesis of DL-form: Korte et al., Tetrahedron 18, 657 (1962); Newman, Chem. Ind. (London) 1963, 372; J. Org. Chem. 29, 1461 (1964). Stereospecific synthesis of the natural D-form: Richardson, J. Chem. Soc. 1964, 5364; of the L-form: Baer, Chiu, Can. J. Chem. 52, 122 (1974).
Properties: Crystals, mp 86-87°.
Melting point: mp 86-87°
Derivative Type: Hydrochloride
Molecular Formula: C8H17NO3.HCl
Molecular Weight: 211.69
Percent Composition: C 45.39%, H 8.57%, N 6.62%, O 22.67%, Cl 16.75%
Properties: Needles from ethanol + acetone, dec 191-193°. [a]D20 +49.5° (c = 10.0); [a]D20 +53.4° (c = 2.1 in ethanol).
Optical Rotation: [a]D20 +49.5° (c = 10.0); [a]D20 +53.4° (c = 2.1 in ethanol)
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