60. Acetobromglucose

Nomenclature

CAS number: 572-09-8
α-d-Glucopyranosyl bromide 2,3,4,6-tetraacetate; α-acetobromoglucose; 2,3,4,6-tetraacetyl-α-d-glucopyranosyl bromide.
C14H19BrO9; mol wt 411.20.
C 40.89%, H 4.66%, Br 19.43%, O 35.02%.

Description and references

Prepd by the action of hydrogen bromide upon anhydrous glucose in acetic anhydride: Redemann, Niemann, Org. Synth. coll. vol. III, 11 (1955). See also Fischer, Ber. 49, 584 (1916); Freudenberg, Ber. 60, 241 (1927); Gattermann-Wieland, Praxis des Organischen Chemikers (de Gruyter, Berlin, 40th ed., 1961) p 340.

Chemical structure

Properties

Crystals from isopropyl ether, mp 88-89°. [α]D19 +199.3° (c = 3 in chloroform); [α]D15 +230.3° (c = 9 in benzene). Best stored in a vacuum desiccator. Dec on contact with water. One gram dissolves in 20 ml absolute ethanol, more soluble in methanol. Freely sol in ether, chloroform, acetone, ethyl acetate, benzene. Slightly sol in petr ether.