942428-83-3

Basic information

• Product Name: 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate
• Synonyms: 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate
• CAS NO: 942428-83-3
• Molecular Weight: 519.428
• Mol File: 942428-83-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate(942428-83-3)
• EPA Substance Registry System: 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate(942428-83-3)

Safety Data

• Hazardous Substances Data: 942428-83-3(Hazardous Substances Data)

Upstream product

• 83-87-4 D-glucose pentaacetate 
• 61881-19-4 2,2,2-trifluoro-N-phenyl-acetimidoyl chloride 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 

Downstream Products

• 3180-74-3 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 74950-95-1 4-(Methoxycarbonyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 105260-61-5 p-Methoxycarbonylphenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 
• 2872-65-3 p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 72500-10-8 methyl 3-methoxy-4-{[(2S,3R,4S,5R,6R)-3,4,5-tris(acetoxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}benzoate 
• 1293384-36-7 methyl 3-methoxy-4-(6'-O-trityl-β-D-glucopyranosyloxy)benzoate 
• 1293384-38-9 allyl 3-methoxy-4-(2',3',4'-tri-O-benzyl-β-D-glucopyranosyloxy)benzoate 
• 1293384-37-8 methyl 3-methoxy-4-(2',3',4'-tri-O-benzyl-β-D-glucopyranosyloxy)benzoate 
• 1293384-35-6 methyl 3-methoxy-4-(2',3',4'-tri-O-benzyl-6'-O-trityl-β-D-glucopyranosyloxy)benzoate 
• 72500-11-9 methyl 3-methoxy-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(hydroxy)methyl]oxan-2-yl]oxy}benzoate 
• 105330-52-7 (+)-catechin 4'-O-β-D-glucopyranoside 
• 105330-51-6 (+)-catechin 3'-O-β-D-glucopyranoside 
• 88126-53-8 (+)-epicatechin 5-O-β-D-glucopyranoside 
• 1209469-11-3 3,5,7,3',2'',3'',4'',6''-octa-O-acetyl-(+)-catechin 4'-O-β-D-glucoside 

Relevant articles and documents

C-glycosylated pyrroles and their application in dipyrromethane and porphyrin synthesis

Pyrrole C-glycosylated in either the 2-or the 3-position could be prepared by the acid-catalyzed reaction between trichloroacetimidate glycosyl donors and pyrrole, or N-phenyl-tri?uoroacetimidate glucosyl donor and N-TIPS pyrrole, respectively. Pyrroles c

3-(Dimethylamino)-1-propylamine: A cheap and versatile reagent for removal of byproducts in carbohydrate chemistry

Inexpensive 3-(dimethylamino)-1-propylamine (DMAPA) was found to be effective in anomeric deacylation reactions giving 1-O deprotected sugars in high yield as precursors for the formation of imidate glycosyl donors. DMAPA was also found to be useful for removing excess reagents such as benzoyl chloride, tosyl chloride, and 2,2,2-trifluoro-N-phenylacetimidoyl chloride. The deacylation reaction could be conducted in moist THF and did not require chromatographic purification since an acidic wash was sufficient to remove excess reagent and the formed byproduct.

First O-glycosylation of hydroxamic acids

(Chemical Equation Presented) The first O-glycosylation of hydroxamic acids is reported. This process involves the use of glycosyl N-phenyl trifluoroacetimidates as glycosyl donors in the presence TMSOTf and 4 A molecular sieves in dichloromethane. Under