408506-92-3

Upstream product

• 221190-01-8 o-nitrobenzyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 1486-47-1 3,4,5-tris(benzyloxy)benzoyl chloride 
• 1486-48-2 3,4,5-tribenzyloxybenzoic acid 
• 408506-91-2 1-O-(tri-O-benzylgalloyl)-2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 

Downstream Products

• 408506-93-4 1,3-di-O-(tri-O-benzylgalloyl)-2-O-benzyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

First total synthesis of the natural product 1,3-di-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl-β-D-glucopyranoside

A straightforward synthesis of the natural product 1,3-di-O-galloyl-4,6-O-(S)-hexahydroxy-diphenoyl-β-D-glucopyranoside (7) was achieved based on a regio- and stereoselective galloylation of the 1,3-diol derivative of D-glucopyranose 2 to the β-D-glucopyranoside 3. Subsequent acylation of monoester 3 to the diester 4 followed by the removal of the benzylidene protecting group led to the formation of the corresponding 4,6-diol derivative of D-glucopyranoside 5. A further double esterification of the (rac)-hexabenzyloxydiphenic acid with the appropriately substituted 4,6-diol derivative of D-glucopyranoside 5 allowed us to assemble the carbon framework of the target 7. Hydrogenolysis of the tetraester 6 as the precursor of the target compound over palladium on charcoal gave the natural product 7.