799271-48-0

Basic information

• Product Name: N¹-acetoxy-2,2,5,5-tetramethylpyrrolidin-3-oyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosylamine
• CAS NO: 799271-48-0
• Molecular Weight: 748.916
• Mol File: 799271-48-0.mol

Chemical Properties

• CAS DataBase Reference: N¹-acetoxy-2,2,5,5-tetramethylpyrrolidin-3-oyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N¹-acetoxy-2,2,5,5-tetramethylpyrrolidin-3-oyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosylamine(799271-48-0)
• EPA Substance Registry System: N¹-acetoxy-2,2,5,5-tetramethylpyrrolidin-3-oyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosylamine(799271-48-0)

Safety Data

• Hazardous Substances Data: 799271-48-0(Hazardous Substances Data)

Upstream product

• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 524036-45-1 1-N-acetoxy-3-carbamoyl-2,2,5,5-tetramethylpyrrolidine 
• 65594-24-3 1-hydroxy-2,2,5,5-tetramethyl-pyrroline-3-carboxamide 

Relevant articles and documents

Synthesis and enzyme-catalyzed hydrolysis of a radical-masked glycosylated spin-label reagent

N1-Acetoxy-2,2,6,6-tetramethylpiperidin-4-yl 2,3,4,6-tetra-O-benzyl-α- and -β-d-glucopyranosides (3-α, β) and N1-acetoxy-2,2,5,5-tetramethylpyrrolin-3-oyl 2,3,4,6-tetra-O-benzyl-α- and -β-d-glucopyranosylamines (9-α, β) were synthesized in good yield by Schmidt's glycosylation method. Their subsequent O-debenzylation was proceeded successfully to give the desired products 1-α, and 1-β in good yield, and 2-α in a low yield, without 2-β by only short-timed hydrogenolysis in the presence of palladium-on-carbon (Pd-C) in a CHCl3-MeOH solvent system that included concentrated HCl. Upon enzyme-catalyzed hydrolysis, only 2-α was hydrolyzed by the esterase, while both of 1-α and 1-β were not hydrolyzed by any other enzyme such as lipase. These 2-α can likely be used as a new water-soluble radical-masked glycosylated spin-label reagent.