866325-70-4

Basic information

• Product Name: allyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside
• Synonyms: allyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside
• CAS NO: 866325-70-4
• Molecular Weight: 532.547
• Mol File: 866325-70-4.mol

Chemical Properties

• CAS DataBase Reference: allyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: allyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside(866325-70-4)
• EPA Substance Registry System: allyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside(866325-70-4)

Safety Data

• Hazardous Substances Data: 866325-70-4(Hazardous Substances Data)

Upstream product

• 492-61-5 β-D-glucose 
• 1228755-40-5 C₄₆H₄₆O₉Si 
• 10343-15-4 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester 
• 2595-07-5 allyl β-D-glucopyranoside 
• 866325-71-5 allyl 6-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside 
• 98-88-4 benzoyl chloride 

Downstream Products

• 1159181-14-2 2-propen-1-yl 2,3,4-tri-O-benzoyl-6-deoxy-6-fluoro-β-D-glucopyranoside 
• 1159181-13-1 2,3,4-tri-O-benzoyl-6-O-(2-propen-1-yl)-β-D-glucopyranosyl fluoride 
• 169557-99-7 2,3,4-tri-O-benzoyl-1-deoxy-1-(2,2,2-trichloro-1-iminoethoxy)-α-D-glucopyranuronate, methyl ester 
• 84954-92-7 cinnamyl 6-O-(α-L-arabinopyranosyl)-β-D-glucopyranoside 
• 866325-75-9 4-methoxycinnamyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-β-D-glucopyranoside 

Relevant articles and documents

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The Rosavin framework could be constructed with either phenylboronic acids, the protected arabinopyranosyl bromide 4 or the protected xylopyranosyl bromide 5, along with allyl O-β-d-glucopyranoside 7 that could be easily prepared based on direct β-glucosidation between allyl alcohol and d-glucose using the immobilized β-glucosidase (EC 3.2.1.21). The key reaction was the Pd(II)-catalyzed Mizoroki-Heck type reaction between allyl β-d- glucopyranoside congeners 9 or 10 and arylboronic acids. Deprotection of the coupling products afforded synthetic Rosavin 1, 4-methoxycinnamyl 6-O-(α-l-arabinopyranosyl)-β-d-glucopyranoside 2, and cinnamyl 6-O-(β-d-xylopyranosyl)-β-d-glucopyranoside 3, which were identical with the natural products in respect to the specific rotation and spectral data.