569359-01-9

Basic information

• Product Name: N-benzyl-C-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-methanesulfonamide
• Synonyms: N-benzyl-C-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-methanesulfonamide
• CAS NO: 569359-01-9
• Molecular Weight: 443.518
• Mol File: 569359-01-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-benzyl-C-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-methanesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyl-C-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-methanesulfonamide(569359-01-9)
• EPA Substance Registry System: N-benzyl-C-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-methanesulfonamide(569359-01-9)

Safety Data

• Hazardous Substances Data: 569359-01-9(Hazardous Substances Data)

Upstream product

• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 100-46-9 benzylamine 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 3989-45-5 N-benzylmethanesulfonamide 

Relevant articles and documents

Cerium(III) chloride-mediated reactions of sulfonamide dianions

Presented here is the first report on the ability of cerium(III) chloride to mediate high-yielding and, oftentimes, highly diastereoselective additions of N-benzyl-α, N-dilithio methanesulfonamide to aldehydes and ketones of biological importance. Smooth addition was effected to base-sensitive substrates such as Fmoc-protected alaninal, citral, 5-cholesten-3-one, uridine 5′-aldehyde, 3′-ketouridine, and 3′-ketothymidine. The reaction was chemoselective for aldehydes in the presence of nitriles. Acetoxy groups are labile and thus not suitable protecting groups for alcohols under these conditions. N-Benzyl-α, N-dilithio methanesulfonamide was found to be of sufficient basicity to cause enolate formation with sensitive substrates, such as 1-phenylacetone. However, the addition of cerium(III) chloride mediated the basicity of the dianion and suppressed enolate formation in these cases. Further, cerium(III) has general utility for the addition of various N-aliphatic/aromatic methanesulfonamide dianions to 3′-ketouridine.