8077. Quinovose

Nomenclature

CAS number: 7658-08-4
6-Deoxy-d-glucose; d-glucomethylose; d-isorhamnose; d-epirhamnose; isorhodeose; epifucose; chinovose.
C6H12O5; mol wt 164.16.
C 43.90%, H 7.37%, O 48.73%.

Description and references

Isoln from cinchona bark: Freudenerg, Ber. 62, 373 (1929). Identity with d-glucomethylose: Votocek, Rác, Collect. Czech. Chem. Commun. 1, 239 (1929). Structure: Karrer, Boettcher, Helv. Chim. Acta 36, 570 (1953). Synthesis from 6-O-p-tolylsulfonyl-d-glucose: Schmidt, “6-Deoxy-α-d-glucose” in Methods in Carbohydrate Chemistry vol. I, R. L. Whistler, M. L. Wolfrom, Eds. (Academic Press, New York, 1962) pp 198-201. Alternate facile synthesis: V. K. Srivastava, L. M. Lerner, Carbohydr. Res. 64, 263 (1978).

Chemical structure

Properties

Crystals from ethyl acetate, mp 146°. [α]D20 +73° (5 min) → +30° (3 hr, final) (c = 8.3 in water). Sol in water, ethanol. Practically insol in ether, acetone.