288402-11-9

Basic information

• Product Name: N-(β-D-glucopyranosyl)-N'-(p-methylphenyl)thiourea
• Synonyms: N-(β-D-glucopyranosyl)-N'-(p-methylphenyl)thiourea
• CAS NO: 288402-11-9
• Molecular Weight: 328.389
• Mol File: 288402-11-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-(β-D-glucopyranosyl)-N'-(p-methylphenyl)thiourea(CAS DataBase Reference)
• NIST Chemistry Reference: N-(β-D-glucopyranosyl)-N'-(p-methylphenyl)thiourea(288402-11-9)
• EPA Substance Registry System: N-(β-D-glucopyranosyl)-N'-(p-methylphenyl)thiourea(288402-11-9)

Safety Data

• Hazardous Substances Data: 288402-11-9(Hazardous Substances Data)

Upstream product

• 7284-37-9 D-glucopyranosyl amine 
• 50802-49-8 β-D-glucopyranosyl isothiocyanate 
• 106-49-0 p-toluidine 
• 463-71-8 thiophosgene 

Downstream Products

• 866416-49-1 N-acetyl-N-(p-methylphenyl)-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiourea 

Relevant articles and documents

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.