473876-57-2

Upstream product

• 690663-51-5 methyl 2,3,4-tri-O-acetyl-α-D-gluco-hexodialdo-1,5-pyranoside-6-O-methyloxime 
• 23598-28-9 methyl 2,3,4-tri-O-acetyl-6-aldehydo-α-D-gluco-hexodialdo-1,5-pyranoside 
• 7432-72-6 methyl 2,3,4-tri-O-acetyl-α-D-glucopyranose 
• 7511-40-2 methyl 2,3,4-tri-O-acetyl-6-O-trityl-α-D-glucopyranoside 

Downstream Products

• 473876-58-3 methyl 6-deoxy-6-methoxyamino-α-D-glucopyranoside 

Relevant academic research and scientific papers

Solution and solid-phase chemoselective synthesis of (1-6)-amino(methoxy) di- and trisaccharide analogues.

Disaccharide and trisaccharide mimics containing the amino(methoxy) interglycosidic linkage were obtained by chemoselective condensation of unprotected aldoses in an aqueous environment both in solution and in solid phase.

Synthesis and Conformational Analysis of Novel N(OCH3)-linked Disaccharide Analogues

N(OMe)-linked disaccharide analogues, isosteric to the corresponding natural disaccharides, have been synthesized by chemoselective assembly of unprotected natural monosaccharides with methyl 6-deoxy-6-methoxyamino-α -D-glucopyranoside in an aqueous environment. The coupling reactions were found to be chemo- and stereoselective affording β-(1→6) disaccharide mimics when using Glc and GlcNAc; in the case of Gal, the β-anomer was prevalent (β:α = 7:1). An iterative method for the synthesis of linear N(OMe) oligosaccharide analogues was demonstrated, based on the use of an unprotected monosaccharide building block in which an oxime functionality at C-6 is converted during the synthesis into the corresponding methoxyamino group. The conformational analysis of these compounds was carried out by using NMR spectroscopy, ab initio, molecular mechanics, and molecular dynamics methods. Optimized geometries and energies of fourteen conformers for each compound have been calculated at the B3LYP/631G* level. Predicted conformational equilibria were compared with the results based on NMR experiments and good agreement was found. It appears that N(OMe)-linked disaccharide analogues exhibit a slightly different conformational behavior to their parent natural disaccharides.