620946-82-9

Basic information

• Product Name: (Z)-(2,3,5-tri-O-benzyl-D-ribofuranosylidene)amino methanesulfonate
• Synonyms: (Z)-(2,3,5-tri-O-benzyl-D-ribofuranosylidene)amino methanesulfonate
• CAS NO: 620946-82-9
• Molecular Weight: 511.596
• Mol File: 620946-82-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (Z)-(2,3,5-tri-O-benzyl-D-ribofuranosylidene)amino methanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-(2,3,5-tri-O-benzyl-D-ribofuranosylidene)amino methanesulfonate(620946-82-9)
• EPA Substance Registry System: (Z)-(2,3,5-tri-O-benzyl-D-ribofuranosylidene)amino methanesulfonate(620946-82-9)

Safety Data

• Hazardous Substances Data: 620946-82-9(Hazardous Substances Data)

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 620946-81-8 (Z)-2,3,5-tri-O-benzyl-D-ribonhydroximo-1,4-lactone 
• 620946-65-8 (Z)-2,3,5-tri-O-benzyl-D-ribose oxime 
• 16838-89-4 2,3,5-tri-O-benzyl-D-ribofuranose 

Downstream Products

• 14233-64-8 (3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-dihydro-furan-2-one 

Relevant articles and documents

Glycosylidene carbenes: Part 31. Glycosylidene diaziridines: Stereoselective addition of ammonia and methylamine to lactone oxime sulfonates

The diastereoselectivity of the addition of NH3 and MeNH2 to glyconolactone oxime sulfonates and the structures of the resulting N-unsubstituted and N-methylated glycosylidene diaziridines were The 15N-labelled glucono- and galactono-1,5-lactone oxime mesylates 1* and 9* add NH3 mostly axially (> 3:1; Scheme 4), while the 15N-labelled mannono-1,5-lactone oxime sulfonate 19* adds NH3 mostly equatorially (9:1; Scheme 7). The 15N-labelled mannono-1,4-lactone oxime sulfonate 30* adds NH3 mostly from the exo side (>4:1; Scheme 9). The configuration of the N-methylated pyranosylidene diaziridines 17, 18, 28, and 29 suggests that MeNH2 adds to 1, 9, 19, and 23 mostly to exclusively from the equatorial direction (> 7:3; Schemes 5 and 8). The mannono-1,4-lactone oxime sulfonate 30 adds MeNH2 mostly from the exo side (85:15; Scheme 10), while the ribo analogue 37 adds MeNH2 mostly from the endo side (4:1; Scheme 10). Analysis of the preferred and of the reactive conformers of the tetrahedral intermediates suggests that the addition of the amine to lactone oxime sulfonates is kinetically controlled. The diastereoselectivity of the diaziridine formation is rationalized as the result of the competing influences of intramolecular H-bonding during addition of the amines, steric interactions (addition of MeNH2), and the kinetic anomeric effect. The diaziridines obtained from 2,3,5-tri-O-benzyI-D-ribono- and -D-arabinono-1,4-lactone oxime methanesulfonate (42 and 48; Scheme II) decomposed readily to mixtures of 1,4-dihydro-1,2,4,5-tetrazines, pentono-1,4-lactones, and pentonamides. The N-unsubstituted gluco- and galactopyranosylidene diaziridines 2, 4, 6, 8, and 10 are mixtures of two trans-substituted isomers (S/R ca. 19:1, Scheme 2). The main, (S,S)-configured isomers S are stabilised by a weak intramolecular H-bond from the pseudoaxial NH to RO-C(2). The diaziridines 12, derived from GlcNAc, cannot form such a H-bond; the (R,R)-isomer dominates (R/S 85:15; Scheme 3). The 2,3-di-O-benzyl-D-mannopyranosylidene diaziridines 20 and 22 adopt a 4C1 conformation, which does not allow an intramolecular H-bond; they are nearly 1:1 mixtures of R and S diastereoisomers, whereas the 0H5 conformation of the 2,3:5,6-di-O-isopropylidene-D-mannopyranosylidene diaziridines 24 is compatible with a weak, H-bond from the equatorial NH to O-C(2); the (R,R)-isomer is favoured (R/S ≥ 7:3: Scheme 6). The mannofuranosylidene diaziddine 31 completely prefers the (R,R)-configuration (Scheme 9).