97747-56-3

Basic information

• Product Name: cis-verbascoside
• Synonyms: cis-verbascoside
• CAS NO: 97747-56-3
• Molecular Weight: 624.596
• Mol File: 97747-56-3.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: cis-verbascoside(CAS DataBase Reference)
• NIST Chemistry Reference: cis-verbascoside(97747-56-3)
• EPA Substance Registry System: cis-verbascoside(97747-56-3)

Safety Data

• Hazardous Substances Data: 97747-56-3(Hazardous Substances Data)

Upstream product

• 94130-58-2 Arenarioside 
• 61276-17-3 Acteoside 
• 250740-80-8 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 4-O-[(E,Z)-3,4-bis(O-tert-butyldimethylsilyl)caffeoyl]-6-O-(4,4'-dimethoxytrityl)-3-O-(α-L-rhamnopyranosyl)-β-D-glucopyranose 
• 253790-75-9 3,4-di(benzyloxy)phenethyl 2,6-di-O-acetyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside 
• 253790-73-7 3,4-di(benzyloxy)phenethyl 2,6-di-O-acetyl-3-O-allyl-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside 
• 253790-74-8 3,4-di(benzyloxy)phenethyl 2,6-di-O-acetyl-4-O-(3,4-di-O-benzylcaffeoyl)-β-D-glucopyranoside 
• 253790-71-5 3,4-di(benzyloxy)phenethyl 2,4-di-O-acetyl-3-O-allyl-6-O-trityl-β-D-glucopyranoside 
• 253790-70-4 3,4-di(benzyloxy)phenethyl 3-O-allyl-6-O-trityl-β-D-glucopyranoside 
• 253790-68-0 3,4-di(benzyloxy)phenethyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside 
• 253790-72-6 3,4-di(benzyloxy)phenethyl 2,6-di-O-acetyl-3-O-allyl-β-D-glucopyranoside 
• 253790-69-1 3,4-di(benzyloxy)phenethyl 3-O-allyl-β-D-glucopyranoside 
• 253790-67-9 2,4,6-tri-O-acetyl-3-O-allyl-α-D-glucopyranosyl chloride 
• 39698-00-5 acetyl 2,4,6-tri-O-acetyl-3-O-allyl-β-D-glucopyranoside 
• 54429-62-8 (E)-3-(3,4-bis(benzyloxy)phenyl)acrylic acid 

Downstream Products

• 90985-64-1 deacylverbascoside dimethyl ether 
• 64142-09-2 acteoside tetramethyl ether 
• 90985-64-1 3,4-dihydroxy-β-phenethyl-O-α-L-rhamnopyranosyl-(1<*>3)-β-D-glucopyranoside dimethyl ether 
• 84744-28-5 calceolarioside A 
• 61303-13-7 Isoacteoside 
• 86495-62-7 per-O-acetyl-verbascoside 
• 10597-60-1 hydroxytyrosol 
• 3843-74-1 Methyl caffeate 
• 2280-44-6 D-Glucose 
• 73-34-7 L-rhamnose 
• 3615-41-6 L-Rhamnose 
• 50-99-7 D-glucose 

Relevant articles and documents

NINE PHENETHYL ALCOHOL GLYCOSIDES FROM STACHYS SIEBOLDII

Three new phenethyl alcohol glycosides together with six known compounds have been isolated from the leaves of Stachys sieboldii.On the basis of chemical and spectral analyses, the structures of three new compounds named stachysosides A, B and C have been established as 2-(3,4-dihydroxyphenyl)ethyl O-α-L-arabinopyranosyl-(1->2)-α-L-rhamnopyranosyl-(1->3)-4-O-E-caffeoyl-β-D-glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl O-α-L-arabinopyranosyl-(1->2)-α-L-rhamnopyranosyl-(1->3)-4-O-E-feruloyl-β-D-glucopyranoside and 2-(3-hydroxy-4-methoxyphenyl)ethyl O-α-L-arabinopranosyl-(1->2)-α-L-rhamnopyranosyl-(1->3)-4-O-E-feruloyl-β-D-glucopyranoside, respectively.

An Approach to the Synthesis of Electron-Rich and Hindered Esters and Its Application to the Synthesis of Acteoside

Electron-rich esters are ubiquitously distributed in natural products and play a central role in bioactivities. Herein, we disclose an efficient, mild, and general esterification approach to the synthesis of these esters by employing gold(I)-catalyzed acylation reaction with alkyne-tethered mixed anhydrides and alcohols. This method can be applied to ester-bond formation in complex substrates and facilitates efficient synthesis of acteoside, which belongs to the family of phenylethanoid glycosides and possesses a broad range of bioactivities.

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).