33204-32-9

Basic information

• Product Name: beta-D-glucopyranosylurea
• Synonyms: beta-D-glucopyranosylurea;1-(β-D-Glucopyranosyl)urea;1-β-D-Glucopyranosylurea;N-(β-D-Glucopyranosyl)urea;N-Carbamoyl-β-D-glucopyranosylamine
• CAS NO: 33204-32-9
• Molecular Formula: C₇H₁₄N₂O₆
• Molecular Weight: 222.19586
• EINECS: 251-404-0
• Mol File: 33204-32-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 208-209 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• Boiling Point: 534.8°Cat760mmHg
• Flash Point: 277.3°C
• Appearance: /
• Density: 1.65g/cm³
• PKA: 11.51±0.70(Predicted)
• CAS DataBase Reference: beta-D-glucopyranosylurea(CAS DataBase Reference)
• NIST Chemistry Reference: beta-D-glucopyranosylurea(33204-32-9)
• EPA Substance Registry System: beta-D-glucopyranosylurea(33204-32-9)

Safety Data

• Hazardous Substances Data: 33204-32-9(Hazardous Substances Data)

Upstream product

• 2280-44-6 D-Glucose 
• 57-13-6 urea 
• 50-99-7 D-glucose 
• 7664-93-9 sulfuric acid 
• 1171112-63-2 N-(4-chlorobenzoyl)-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)urea 
• 1171112-65-4 C₂₂H₂₅ClN₂O₁₁ 
• 1050350-24-7 N-(4-acetoxybenzoyl)-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)urea 
• 1050350-27-0 N-(4-phenylbenzoyl)-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)urea 
• 1050350-30-5 N-(4-methylbenzoyl)-N'-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)urea 
• 1050349-33-1 N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N'-(4-tert-butylbenzoyl)urea 
• 1050349-39-7 N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N'-(4-trifluoromethyl-benzoyl)urea 
• 1050350-32-7 C₂₃H₂₈N₂O₁₁ 
• 1050350-34-9 C₂₉H₃₂N₂O₁₁ 
• 1050350-36-1 C₂₆H₂₈N₂O₁₁ 

Downstream Products

• 122452-54-4 N-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)urea 

Relevant articles and documents

Efficient preparation of β-D-glucosyl and β-D-mannosyl ureas and other N-glucosides in carbohydrate melts

Sugar melts or solvent-free systems have been used to react simple unprotected hexoses at the C-1 atom with urea and urea derivatives to sugar-ureides by acid catalysis and with short reaction times. In one step, β-d-glucosyl- and β-d-mannosyl urea 2a/b were obtained in high yields. d-Galactose 6, N-acetyl-d-glucosamine 7, l-rhamnose 8 and 2-deoxy-d-glucose 9 were converted likewise to glycosyl ureas. Additionally, urea-related nucleophiles were investigated as melt components. N,N′-Ethylene urea 15, N,N′-allylurea 16 and ethyl carbamate 18 were β-selectively converted with d-glucose in good yield, giving the corresponding N-glycosides. Under these conditions, however, the condensation product with N-octylurea 17 was not accessible.

CARBOHYDRATE-UREA-PHENOL-BASED ADHESIVES: TRANSIENT FORMATION OF MONO- AND DI-D-GLUCOSYLUREA

The chemistry of the acid stage of the synthesis of carbohydrate-based adhesives has been investigated.The sulfuric acid-catalyzed reactions of D-glucose with urea in a phenol-water solution provided both N-β-D-glucopyranosylurea and N,N'-di-β-D-glucopyranosylurea.These compounds have been isolated from the resin as perbenzoylated derivatives, and compared spectroscopically with authentic samples.The D-glucosylureas are transient products whose combined yields approach 35percent of the carbohydrate fraction during the initial stages of resin synthesis.Only traces of 5-(hydroxymethyl)-2-furaldehyde, levulinic acid, and formic acid were detected in the resin mixture, suggesting that the classical dehydration pathway is not a major route for the disappearance of D-glucose.