N4-beta-D-Glucosylsulfanilamide
Title: N4-b-D-Glucosylsulfanilamide
CAS Registry Number: 53274-53-6
CAS Name: 4-(b-D-Glucopyranosylamino)benzenesulfonamide
Additional Names: N4-b-d-glucosidosulfanilamide; sulfanilamide-d-glucoside; N-p-sulfamylphenyl-D-glucosylamine
Trademarks: Prontoglucal; Prontoglukal
Molecular Formula: C12H18N2O7S
Molecular Weight: 334.35
Percent Composition: C 43.11%, H 5.43%, N 8.38%, O 33.50%, S 9.59%
Literature 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).
Properties: Fine needles from aq ethanol, mp 204°. [a]D22 -117° (c = 0.9 in pyridine); [a]D22 -128° (c = 0.9 in water).
Melting point: mp 204°
Optical Rotation: [a]D22 -117° (c = 0.9 in pyridine); [a]D22 -128° (c = 0.9 in water)
 
Derivative Type: 2,3,4,6-Tetraacetate
Molecular Formula: C20H26N2O11S
Molecular Weight: 502.49
Percent Composition: C 47.80%, H 5.22%, N 5.57%, O 35.02%, S 6.38%
Properties: Crystals from ethanol, mp 204°. [a]D22 -81° (pyridine).
Melting point: mp 204°
Optical Rotation: [a]D22 -81° (pyridine)
 
Derivative Type: N,N¢,2,3,4,6-Hexaacetate
Molecular Formula: C24H30N2O13S
Molecular Weight: 586.57
Percent Composition: C 49.14%, H 5.16%, N 4.78%, O 35.46%, S 5.47%
Properties: Crystals from ethanol, mp 115°.
Melting point: mp 115°
 
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Synthetic); Sulfonamides.
 
 
Status: This monograph has been retired and is no longer subject to revision or update.

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