1241901-08-5

Upstream product

• 1241901-05-2 N,N'-bis(1-O-allyl-4,6-O-benzylidene-2,3-N,O-carbonyl-2-deoxy-α-D-glucopyranos-2-yl)urea 
• 1241901-03-0 allyl 4,6-O-benzylidene-2-deoxy-2-[(p-nitrophenoxy)carbonylamino]-α-D-glucopyranoside 
• 191925-41-4 allyl 2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 

Downstream Products

• 1241901-12-1 N-[3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-1-O-allyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranos-2-yl]-N'-(1-O-allyl-4,6-O-benzylidene-2,3-N,O-carbonyl-2-deoxy-α-D-glucopyranos-2-yl)urea 
• 1241901-15-4 C₃₄H₃₈N₂O₁₂ 

Relevant academic research and scientific papers

Versatile and self-assembling urea-linked neosaccharides from sugar aminoalcohols

The increasing interest in urea compounds as self-assembling molecules, ion transporters and organocatalysts prompted several efforts towards synthetic urea-linked glycomimetics. In this frame we studied in details a novel two steps dimerization reaction of sugar vicinal aminoalcohol building blocks, opening a synthetic path to a series of urea-linked neosaccharides. Glucosamine neodisaccharide possessing an oxazolidinone-urea-oxazolidinone system could be transformed into both cyclic and higher linear neosaccharides. Furthermore, a series of six urea-linked glucosamine and galactosamine neodisaccharides was tested for self-assembling properties by measuring NMR spectra at different temperatures and concentrations as well as by gelation of several organic solvents.

A urea-linked glucosamine dimer as a building block for the synthesis of linear and cyclic neosaccharides

A novel urea-linked glucosamine dimer was obtained through a modification of the standard oxazolidinone closure reaction on a 2,3-amino alcohol monomer and fully characterized by NMR spectroscopy and by molecular mechanics and dynamics techniques. A mechanism was proposed for the dimerization reaction that was based on the formation of a 2,3-bis[(p-nitrophenoxy)carbonyl] intermediate, Chemoselective manipulations on the orthogonal protecting group pattern of the dimer - especially on its unprecedented oxazolidinone-urea-oxazolidinone system - gave an alcohol building block that was useful for access to higher linear and cyclic neosaccharides, The conformational features and 3Dcharacterization of a novel carbamate-linked neodisaccharide macrocycle was accomplished through molecular mechanics and dynamics calculations.