50802-49-8

Basic information

• Product Name: N-(thioxomethylidene)-beta-D-glucopyranosylamine
• Synonyms: beta-D-glucopyranosylamine, N-carbonothioyl-; beta-D-Glucopyranosylisothiocyanate; N-(Thioxomethylene)-beta-D-glucopyranosylamine
• CAS NO: 50802-49-8
• Molecular Formula: C₇H₁₁NO₅S
• Molecular Weight: 221.2309
• Mol File: 50802-49-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 492.9°C at 760 mmHg
• Flash Point: 251.9°C
• Density: 1.75g/cm³
• Vapor Pressure: 8.8E-12mmHg at 25°C
• Refractive Index: 1.677
• CAS DataBase Reference: N-(thioxomethylidene)-beta-D-glucopyranosylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(thioxomethylidene)-beta-D-glucopyranosylamine(50802-49-8)
• EPA Substance Registry System: N-(thioxomethylidene)-beta-D-glucopyranosylamine(50802-49-8)

Safety Data

• Hazardous Substances Data: 50802-49-8(Hazardous Substances Data)

Upstream product

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

Downstream Products

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

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.

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.