Title: Digitoxose
CAS Registry Number: 527-52-6
CAS Name: 2,6-Dideoxy-D-ribo-hexose
Additional Names: 2-desoxy-D-altromethylose; 2,6-didesoxy-D-allose
Molecular Formula: C6H12O4
Molecular Weight: 148.16
Percent Composition: C 48.64%, H 8.16%, O 43.19%
Literature References: Obtained by mild acid hydrolysis of the glycosides digitoxin, gitoxin and digoxin: Cloetta, Arch. Exp. Pathol. Pharmakol. 88, 113 (1920); 112, 261 (1926); Windaus, Stein, Ber. 61, 2436 (1928); Kraft, Arch. Pharm. 250, 118 (1912); Mannich et al., ibid. 268, 453 (1930); Smith, J. Chem. Soc. 1930, 508; 1931, 23. Configuration: Micheel, Ber. 63, 347 (1930). Structure: S. F. Dyke, The Carbohydrates (Interscience, New York, 1960) p 104. Synthesis: Gut, Prins, Helv. Chim. Acta 30, 1223 (1947); Bolliger, Ulrich, ibid. 35, 93 (1952). Stereochemical study: S. Tsukamoto et al., J. Chem. Soc. Perkin Trans. 1 1988, 2621. Review: R. C. Elderfield in W. W. Pigman, M. L. Wolfrom, Advances in Carbohydrate Chemistry vol. I (Academic Press, New York, 1945) pp 159-164.
Properties: Crystals from methanol + ether, from ethyl acetate or from acetone + ether, mp 112°. [a]D17 +46.3° (in water); [a]D20 +39.1° (in methanol); [a]D18 +27.9° ® +43.3° (after 24 hrs in pyridine). Freely sol in water; sol in acetone, ethanol. Practically insol in ether.
Melting point: mp 112°
Optical Rotation: [a]D17 +46.3° (in water); [a]D20 +39.1° (in methanol); [a]D18 +27.9° ® +43.3° (after 24 hrs in pyridine) |