50802-49-8

Upstream product

• 14152-97-7 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate 
• 7284-37-9 D-glucopyranosyl amine 
• 463-71-8 thiophosgene 

Downstream Products

• 368886-89-9 (1,2-dideoxy-β-D-glucopyranoso)[1,2-d]-1,3-oxazolidine-2-thione 
• 288402-11-9 N-(β-D-glucopyranosyl)-N'-(p-methylphenyl)thiourea 
• 76799-04-7 1-Benzyl-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-thiourea 

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.

Simple and efficient synthesis of O-unprotected glycosyl thiourea and isourea derivatives from glycosylamines

Practical, facile and high-yielding one-pot syntheses of different O-unprotected glycopyranosyl thioureas and thioureido bolaamphiphiles (two-step synthesis) and of 2-amino-4,5-dihydro-(1,2-dideoxy-β-D-glucopyranoso)[1,2- d]oxazoles (three-step synthesis) from glycopyranosylamines are reported. The method involves the preparation of O-unprotected β-D-gluco (and D-galacto)pyranosyl isothiocyanates which are in equilibrium with the corresponding 1,2-cyclic thiocarbamates, coupling with amines to afford glycosyl thioureas and treatment with yellow mercury (II) oxide to give trans-fused bicyclic isoureas. A D-gluco trehazolin analogue is prepared in this way. In situ transformation of N,N-dialkyl, N′-glucopyranosyl thioureas into the corresponding ureas is also reported.

Expeditious synthesis of cyclic isourea derivatives of β-D-glucopyranosylamine

2-(Alkylamino, dialkylamino, arylamino)tetrahydropyrano[2,3-d]oxazoles are prepared in good yield by a one-pot three-step synthesis from O-unprotected β-D-glucopyranosylamine, by its transformation into glucopyranosyl isothiocyanate in dioxane-water, coupling with amines, and reaction of the corresponding thioureas with yellow mercury(II) oxide in the same reaction medium. In the case of diethylamine prolonged reaction time during the last step, with an extra portion of yellow HgO, led to N,N-diethyl-N′-(β-D-glucopyranosyl)urea in a one-pot four-step synthesis. 2-(β-D-Glucopyranosylamino)tetrahydropyrano[2,3-d]oxazole, an analogue of trehazolin, is obtained in good yield by cyclocondensation of 1,3-bis(β-D-glucopyranosyl)thiourea.

A practical one-pot synthesis of O-unprotected glycosyl thioureas

An expeditious and high-yielding one-pot procedure to prepare different types of O-unprotected N-β-D-glycopyranosyl, N′-substituted thioureas and di-β-D-glucopyranosyl thioureido bolaamphiphiles from β-D-glycopyranosylamines via O-unprotected glycopyranosyl isothiocyanates has been developed.