753025-65-9

Upstream product

• 676530-89-5 allyl 2-O-(2-azidomethyl)benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 339276-12-9 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate 
• 289712-58-9 2-(azidomethyl)benzoyl chloride 
• 93382-48-0 allyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 753025-63-7 allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-(2-azidomethyl)benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 

Downstream Products

• 753025-67-1 allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-4,6-di-O-acetyl-2-O-(2-azidomethyl)benzoyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of a typical glucuronide-containing saponin, 28-O-β-D- glucopyranosyl oleanate 3-O-β-D-galactopyranosyl-(1→2)-[β-D- glucopyranosyl-(1→3)]-β-D-glucuronopyranoside

28-O-β-D-Glucopyranosyl oleanate 3-O-β-D-galactopyranosyl- (1→2)-[β-D-glucopyranosyl-(1→3)]-β-D-glucuronopyranoside (1), a structurally typical glucuronide-containing triterpene saponin isolated from Aralia dasyphylla, was concisely synthesized in linear nine steps and 26% overall yield. The key features of the synthesis are: (1) attachment of the 28-glucosyl ester ahead of assembly of the 3-O-sugar chain; (2) elaboration of the glucuronide residue at a later stage via the TEMPO-mediated selective oxidation; (3) installation of 2-(azidomethyl)benzoyl group as a benzoylic neighboring participating group which is selectively removed afterwards for synthesis of the 1→2 sugar linkage.