4889. Idose

Nomenclature

CAS number: 2152-76-3
C6H12O6; mol wt 180.16.
C 40.00%, H 6.71%, O 53.28%.

Description and references

Prepn of d-idose by reduction of d-idonolactone: Fischer, Fay, Ber. 28, 1975 (1895); from d-galactose: Sorking, Reichstein, Helv. Chim. Acta 28, 1 (1945); from tri-O-acetyl-1,6-anhydro-β-d-idopyranose: eidem, ibid. 662. Prepn of l-idose by reduction of l-idonolactone: Fischer, Fay, loc. cit.; by hydrolysis of 1,2-O-isopropylidene-l-idofuranose: Meyer, Reichstein, Helv. Chim. Acta 29, 152 (1946); von Vargha, Ber. 87, 1351 (1954). Improved synthesis: M. Blanc-Muesser, J. Defaye, Synthesis 1977, 568. Structure: S. F. Dyke, The Carbohydrates (Interscience, New York, 1960) p 45. Conformation: Reeves, J. Am. Chem. Soc. 72, 1499 (1950). Review: R. L. Whistler, M. L. Wolfrom, Methods in Carbohydrate Chemistry (Academic Press, New York, 1962) pp 140-145.

Chemical structure

Derivative

d-Form.

Properties

Syrup. [α]D13 +15.8° (c = 2.3).

Derivative

Phenylosazone.
C18H22N4O4; mol wt 358.39.
C 60.32%, H 6.19%, N 15.63%, O 17.86%.

Properties

Yellow needles from alc, mp 168-169°.

Derivative

l-Form.

Properties

Syrup. [α]D20 17.4° (c = 3.6).

Derivative

1,2-O-Isopropylidene-l-idofuranose.

Properties

Plates from ethyl acetate, mp 113-114°. [α]D26 20° (c = 2.7 in methanol).