2931. 6-Desoxy-d-glucosamine

Nomenclature

CAS number: 6018-53-7
2-Amino-2,6-dideoxy-d-glucose; 6-deoxy-d-glucosamine; 2,6-didesoxy-2-amino-d-glucose.
C6H13NO4; mol wt 163.17.
C 44.17%, H 8.03%, N 8.58%, O 39.22%.

Description and references

May be prepd by tosylation of the primary alcohol group of a suitable derivative of d-glucosamine, followed by acetylation and replacement of the tosyl group by iodine, and catalytic cleavage of the halide with Raney nickel in the presence of triethylamine: Morel, Helv. Chim. Acta 41, 1501 (1958).

Chemical structure

Derivative

Hydrochloride.
C6H13NO4.HCl; mol wt 199.63.
C 36.10%, H 7.07%, N 7.02%, O 32.06%, Cl 17.76%.

Properties

Crystals from abs ethanol + ether, dec 172-173°. Shows mutarotation. Final value: [α]D20 +55° (H2O).

Derivative

1,3,4-Tri-O-acetyl-N-acetyl-6-desoxy-β-d-glucosamine.
C14H21NO8; mol wt 331.32.
C 50.75%, H 6.39%, N 4.23%, O 38.63%.

Properties

Crystals from alc, mp 209-210°. [α]D20 +17.5° (chloroform).

Use

In the investigation of amino acid metabolism.