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Upstream product

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

Relevant academic research and scientific papers

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.

Assessment of synthetic methods for the preparation of N-β-d-glucopyranosyl-N′-substituted ureas, -thioureas and related compounds

Preparation of O-peracetylated N-β-d-glucopyranosyl-N′-acyl urea derivatives resulted in the formation of anomeric mixtures under the following conditions: acylation of O-peracetylated β-d-glucopyranosyl urea by acyl chlorides in the presence of ZnCl2 in refluxing CHCl3; addition of O-peracetylated β-d-glucopyranosylamine to acyl isocyanates in acetonitrile at rt; addition of carboxamides to in situ prepared O-peracetylated β-d-glucopyranosyl isocyanate in refluxing toluene. Deprotection of O-peracetylated N-β-d-glucopyranosyl-N′-acyl ureas either under base (NaOMe in MeOH at or below rt) or under acid (KHSO4 or AcCl in MeOH at rt) catalyzed transesterification conditions resulted in unavoidable partial cleavage of the N′-acyl moieties. Reaction of β-d-glucopyranosylammonium carbamate with an isocyanate, isothiocyanate or isoselenocyanate in dry pyridine at rt appears as a general method for the preparation of the corresponding β-d-glucopyranosyl ureas, -thio- and -selenoureas, respectively, inclusive N′-acyl derivatives.

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.