352020-79-2

Upstream product

• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 133697-34-4 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol 
• 137344-41-3 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulopyranose 
• 352020-91-8 methyl 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulopyranoside 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 

Downstream Products

• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 354528-73-7 methyl O-(1'-C-methyl-2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucoside 
• 354528-74-8 methyl O-(1'-C-methyl-2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)-(1'->4)-2,3,6-tri-O-benzyl-α-D-glucoside 
• 354528-75-9 methyl O-(1'-C-methyl-2',3',4',6'-tetra-O-benzyl-α-D-mannopyranosyl)-(1'->4)-2,3,6-tri-O-benzyl-α-D-glucoside 

Relevant academic research and scientific papers

Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols

A series of 1-deoxy-heptulo-2-pyranosyl-glycono-1,5-lactones were synthesized utilizing completely α-selective O-glycosidation of heptenitols. Anomeric configuration of the products was confirmed by 3JC,H coupling measurement and X-ray crystal structural analysis. The benzyl-protected ketosyl saccharides were partly unstable, and glycosidic linkage was prone to cleave under the usual debenzylation conditions. To prevent this, we surveyed various additives for the Pd-catalyzed hydrogenation reaction and found that basic alumina was the most effective.

A facile synthesis of 1′-C-alkyl-α-disaccharides from 1-C-alkyl-hexopyranoses and methyl 1-C-methyl-hexopyranosides

Direct O-glycosidations using the 1-C-alkyl-2,3,4,6-tetra-O-benzyl-hexopyranoses as the glycosyl donors were carried out with a catalytic amount (0.2 equiv.) of trimethylsilyl trifluoromethanesulfonate (TMSOTf). The glycosidations proceeded α-stereoselect

An efficient synthesis of new 1′-C-methyl-α-O-disaccharides using 1-methylenesugars as the glycosyl donors

A series of new 1′-C-methyl-α-disaccharides were firstly synthesized by the directly Lewis acid-catalyzed O-glycosidation of 1-methylenesugars used as glycosyl donors. The O-glycosidation afforded stereospecifically the corresponding 1′-methyl-α-O-glycosides whose configurations were tentatively assigned by the NMR spectra, COSY and the C-H coupling constant 3JH-2′,Me-1′. The O-glycosidation of the acetyl protected 1-methylenesugars showed that the acetyl group at the C-2-O position was not effective to control the stereochemistry of the product by neighboring group participation because of the formation of a tertiary oxycarbenium ion as a stable intermediate.