647832-30-2

Upstream product

• 123487-56-9 pent-4-enyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 3840-30-0 5-(chloromethyl)-1,2,3-trimethoxybenzene 
• 3840-31-1 (3,4,5-trimethoxyphenyl)methanol 
• 128503-36-6 (3aS,5R,6R,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-methyl-2-pent-4-enyloxy-tetrahydro-[1,3]dioxolo[4,5-b]pyran 
• 143706-45-0 4-penten-1-yl 2-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 647832-29-9 1,2-O-(4-penten-1-yl)-orthoacetyl-3,4,6-tri-O-acetyl-α-D-mannopyranose 
• 13242-53-0 acetobromomannose 

Downstream Products

• 647832-33-5 (2R,3R,4R,4aR,10bS)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8,9,10-trimethoxy-2,3,4,4a,6,10b-hexahydro-pyrano[3,2-c]isochromene 
• 647832-31-3 (2R,3R,4R,4aR,10bR)-3,4-Bis-benzyloxy-2-benzyloxymethyl-8,9,10-trimethoxy-2,3,4,4a,6,10b-hexahydro-pyrano[3,2-c]isochromene 

Relevant academic research and scientific papers

Intramolecular C-glycosylation of 2-O-benzylated pentenyl mannopyranosides: Remarkable 1,2-trans stereoselectivity

The IDCP-promoted intramolecular C-glycosylation of pentenyl α-mannopyranosides carrying, at O-2, an activated benzyl group gave, unexpectedly, the 1,2-trans-fused bicyclic product which corresponds to an α-C-aryl mannopyranose derivative. This remarkable, strained C-glycosyl compound was rapidly epimerized to the more stable 1,2-cis product on treatment with BF3·Et2O. The IDCP-reaction product could be elaborated into a 2-(α-C-mannopyranosyl)-3,4,5-trimethoxybenzyl alcohol derivative.