13-04477. N4-β-d-Glucosylsulfanilamide [Archived]

Nomenclature

CAS number: 53274-53-6
4-(β-d-Glucopyranosylamino)benzenesulfonamide; N4-β-d-glucosidosulfanilamide; sulfanilamide-d-glucoside; N-p-sulfamylphenyl-d-glucosylamine; Prontoglucal; Prontoglukal.
C12H18N2O7S; mol wt 334.35.
C 43.11%, H 5.43%, N 8.38%, O 33.50%, S 9.59%.

Description and references

Prepn: Kuhn, Birkofer, Ber. 71, 621 (1938); Bognár, Nánási, J. Chem. Soc. 1953, 1703; Bognár et al., Magy. Kem. Foly. 62, 271 (1956), C.A. 54, 4399g (1960). Structure: Braun et al., J. Org. Chem. 7, 19 (1942).

Chemical structure

Properties

Fine needles from aq ethanol, mp 204°. [α]D22 117° (c = 0.9 in pyridine); [α]D22 128° (c = 0.9 in water).

Derivative

2,3,4,6-Tetraacetate.
C20H26N2O11S; mol wt 502.49.
C 47.80%, H 5.22%, N 5.57%, O 35.02%, S 6.38%.

Properties

Crystals from ethanol, mp 204°. [α]D22 81° (pyridine).

Derivative

N,N′,2,3,4,6-Hexaacetate.
C24H30N2O13S; mol wt 586.57.
C 49.14%, H 5.16%, N 4.78%, O 35.46%, S 5.47%.

Properties

Crystals from ethanol, mp 115°.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Synthetic); Sulfonamides

Status

This monograph has been retired and is no longer subject to revision or update.