250740-76-2

Upstream product

• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 250740-59-1 2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α/β-D-glucopyranosyl trichloroacetimidate 
• 250740-68-2 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-1,2:5,6-di-O-isopro-pylidene-α-D-glucofuranoside 
• 250740-56-8 3,4-di-O-acetyl-β-L-rhamnopyranose 1,2-(ethyl 2-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranose-3-yl) orthoacetate 
• 250740-57-9 ethyl 2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-1-thio-β-D-glucopyranoside 
• 250740-58-0 2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside 
• 250740-54-6 3,4-di-O-acetyl-β-L-rhamnopyranose 1,2-(ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranose-3-yl) orthoacetate 
• 246872-14-0 methyl [3,4-bis(tert-butyldimethylsilyloxy)phenyl]acetate 
• 246872-15-1 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethanol 
• 701-99-5 Phenoxyacetyl chloride 
• 148404-74-4 ethyl 2,3,4-tri-O-benzoyl-1-thio-α-L-rhamnopyranoside 
• 20701-61-5 ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 113893-72-4 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trichloroacetimidate 
• 25379-88-8 2-(3,4-dihydroxyphenyl)acetic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of verbascoside: A dihydroxyphenylethyl glycoside with diverse bioactivity

TMSOTf-mediated condensation of ethyl 4,6-O-benzylidene-1-thio-β-D- glucopyranoside (2) with peracetylated α-L-rhamnopyranosyl trichloroacetimidate donor 3a resulted in the formation of orthoester 4, which, after acetylation, rearranged into ethyl 3-O-(α-L-rhamnopyranosyl)-l- thio-β-D-glucopyranoside derivative 6a. The latter compound was converted into the corresponding trichloroacetimidate donors 8a-b. An alternative approach to trichloroacetimidate 8c commenced with the iodonium ion mediated glycosidation of ethyl 2,3,4-tri-O-benzoyl-1-thio-α-L-rhamnopyranside (15) with 1,2:5,6-diisopropylidene-D-glucofuranose (16) to afford disaccharide 17, which was transformed into 8c in five steps. Condensation of 8a-c with 2- [3,4-di-(tert-butyldimethylsilyloxy)phenyl]ethanol (12) gave, after deacylation, key intermediate 14. Protecting-group manipulation of 14 and subsequent esterification of resulting 22 with 3,4-di-O-tert- butyldimethylsilylcaffeic acid (27) gave, after deprotection, verbascoside (1).