714968-86-2

Basic information

• Product Name: N-(β-D-glucopyranosyl)-N'-phenyl selenourea
• Synonyms: N-(β-D-glucopyranosyl)-N'-phenyl selenourea
• CAS NO: 714968-86-2
• Molecular Weight: 361.256
• Mol File: 714968-86-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-(β-D-glucopyranosyl)-N'-phenyl selenourea(CAS DataBase Reference)
• NIST Chemistry Reference: N-(β-D-glucopyranosyl)-N'-phenyl selenourea(714968-86-2)
• EPA Substance Registry System: N-(β-D-glucopyranosyl)-N'-phenyl selenourea(714968-86-2)

Safety Data

• Hazardous Substances Data: 714968-86-2(Hazardous Substances Data)

Upstream product

• 4426-68-0 phenyl isoselenocyanate 
• 103-70-8 Formanilid 
• 7284-37-9 D-glucopyranosyl amine 

Relevant articles and documents

Synthesis of sugar-derived isoselenocyanates, selenoureas, and selenazoles

Aryl, alkyl, and sugar-derived isoselenocyanates were prepared by a one-pot procedure starting from the corresponding formamides, using triphosgene as a dehydrating agent, triethylamine, and black selenium powder. The preparation of sugar selenoureas by coupling of O-protected sugar-derived isoselenocyanates with different amines, and by coupling of unprotected glycopyranosyl amines with phenyl isoselenocyanate was also accomplished. The synthesis of a glucopyranos-2-yl-selenazole starting from O-protected 2-amino-2-deoxy-d-glucose by coupling with benzoyl isoselenocyanate, Se-alkylation with phenacyl bromide, and acid-catalyzed dehydration is also reported. Unprotected N-(β-d-glucopyranosyl)-N′-phenylselenourea was transformed into a 1,2-trans-fused bicyclic isourea upon treatment with aqueous hydrogen peroxide; the same isourea was prepared by a one-pot three-step procedure from β-d-glycopyranosylamine by thiophosgenation, coupling with aniline, and HgO-mediated desulfurization.

Synthesis of O-unprotected glycosyl selenoureas. A new access to bicyclic sugar isoureas

β-D-Gluco and mannopyranosyl selenoureas have been prepared by coupling of the corresponding glycosylamines with phenyl isoselenocyanate in aqueous pyridine. Alkyl and aryl isoselenocyanates, and 1,4-phenylene diisoselenocyanate have been obtained from the corresponding formamides with an excess of triphosgene, black selenium and triethylamine. Treatment of the O-unprotected β-D-glucopyranosyl selenourea with aqueous oxygen peroxide afforded a 1,2-trans-fused bicyclic isourea.