676530-89-5

Upstream product

• 93382-48-0 allyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 289712-58-9 2-(azidomethyl)benzoyl chloride 

Downstream Products

• 676530-90-8 allyl 2-O-(azidomethyl)benzoyl-3-O-benzoyl-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 
• 676530-79-3 2-Azidomethyl-benzoic acid (3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzoyloxy-2-(2,2,2-trifluoro-N-phenyl-acetimidoyloxy)-tetrahydro-pyran-3-yl ester 
• 676530-78-2 allyl 4,6-di-O-acetyl-2-O-(2-azidomethyl)benzoyl-3-O-benzoyl-α-D-glucopyranoside 
• 676530-91-9 2-Azidomethyl-benzoic acid (2S,3R,4S,5R,6R)-2-allyloxy-4-benzoyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl ester 
• 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 
• 753025-65-9 allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->3)-2-O-(2-azidomethyl)benzoyl-α-D-glucopyranoside 
• 938434-75-4 3,4,6-tri-O-acetyl-2-O-[2-(azidomethyl)benzoyl]-D-glucopyranosyl trichloroacetimidate 
• 938434-94-7 C₂₇H₄₀O₃C₆H₁₀O₅(C₂H₂O)3C₆H₁₀O₄(C₇H₄O)3 
• 938434-92-5 C₂₇H₄₀O₃C₆H₁₀O₅(C₂H₂O)3COC₆H₃CH₂N₃ 
• 938434-90-3 C₂₃H₂₇N₃O₁₀ 

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.

Facile Synthesis of Ginsenoside Ro

Two concise synthetic routes, being different in the glycosylation sequence, toward ginsenoside Ro (1) are developed. These syntheses feature the elaboration of the glucuronide residue at a later stage via the TEMPO-mediated selective oxidation and the installation of AZMB as a benzoylic neighboring participating group capable of being selectively removed afterward.