866325-74-8

Basic information

• Product Name: cinnamyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-β-D-glucopyranoside
• Synonyms: cinnamyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-β-D-glucopyranoside
• CAS NO: 866325-74-8
• Molecular Weight: 1053.09
• Mol File: 866325-74-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: cinnamyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: cinnamyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-β-D-glucopyranoside(866325-74-8)
• EPA Substance Registry System: cinnamyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-β-D-glucopyranoside(866325-74-8)

Safety Data

• Hazardous Substances Data: 866325-74-8(Hazardous Substances Data)

Upstream product

• 14206-56-5 2,3,4-tri-O-benzoyl-β-L-arabinopyranosyl bromide 
• 866325-72-6 allyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-β-D-glucopyranoside 
• 98-80-6 phenylboronic acid 
• 98-88-4 benzoyl chloride 
• 2595-07-5 allyl β-D-glucopyranoside 
• 866325-70-4 allyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside 
• 866325-71-5 allyl 6-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside 

Downstream Products

• 84954-92-7 cinnamyl 6-O-(α-L-arabinopyranosyl)-β-D-glucopyranoside 

Relevant articles and documents

Synthesis of Rosavin and its analogues based on a Mizoroki-Heck type reaction

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.