354528-74-8

Upstream product

• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 82598-84-3 2,3,4,6-tetra-O-benzyl-D-galactonolactone 
• 352020-79-2 methyl O-(1'-C-methyl-2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-(1'->6)-2,3,4-tri-O-benzyl-α-D-glucoside 
• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 179090-11-0 (3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-one 

Relevant academic research and scientific papers

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.