408506-93-4

Basic information

• Product Name: 1,3-di-O-(tri-O-benzylgalloyl)-2-O-benzyl-β-D-glucopyranoside
• Synonyms: 1,3-di-O-(tri-O-benzylgalloyl)-2-O-benzyl-β-D-glucopyranoside
• CAS NO: 408506-93-4
• Molecular Weight: 1115.24
• Mol File: 408506-93-4.mol

Chemical Properties

• CAS DataBase Reference: 1,3-di-O-(tri-O-benzylgalloyl)-2-O-benzyl-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-di-O-(tri-O-benzylgalloyl)-2-O-benzyl-β-D-glucopyranoside(408506-93-4)
• EPA Substance Registry System: 1,3-di-O-(tri-O-benzylgalloyl)-2-O-benzyl-β-D-glucopyranoside(408506-93-4)

Safety Data

• Hazardous Substances Data: 408506-93-4(Hazardous Substances Data)

Upstream product

• 408506-91-2 1-O-(tri-O-benzylgalloyl)-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 
• 408506-92-3 1,3-di-O-(tri-O-benzylgalloyl)-2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 221190-01-8 o-nitrobenzyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 

Relevant articles and documents

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.