110978-95-5

Basic information

• Product Name: 2-(4-hydroxyphenyl)ethyl 6-O-(E)-(3-methoxy-4-hydroxy)cinnamoyl β-D-glucopyranoside
• Synonyms: 2-(4-hydroxyphenyl)ethyl 6-O-(E)-(3-methoxy-4-hydroxy)cinnamoyl β-D-glucopyranoside
• CAS NO: 110978-95-5
• Molecular Weight: 476.48
• Mol File: 110978-95-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-(4-hydroxyphenyl)ethyl 6-O-(E)-(3-methoxy-4-hydroxy)cinnamoyl β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-hydroxyphenyl)ethyl 6-O-(E)-(3-methoxy-4-hydroxy)cinnamoyl β-D-glucopyranoside(110978-95-5)
• EPA Substance Registry System: 2-(4-hydroxyphenyl)ethyl 6-O-(E)-(3-methoxy-4-hydroxy)cinnamoyl β-D-glucopyranoside(110978-95-5)

Safety Data

• Hazardous Substances Data: 110978-95-5(Hazardous Substances Data)

Upstream product

• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 850786-96-8 (E)-3-methoxy-4-allyloxycinnamoyl chloride 
• 190122-97-5 [1-(4-allyloxyphenyl)]ethyl β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 
• 190123-33-2 (E)-3-(4-Allyloxy-3-methoxy-phenyl)-acrylic acid (2R,3R,4S,5R,6R)-6-[2-(4-allyloxy-phenyl)-ethoxy]-4,5-bis-(2-chloro-acetoxy)-2-(2-chloro-acetoxymethyl)-tetrahydro-pyran-3-yl ester 
• 190123-02-5 (E)-3-[4-(2-Chloro-acetoxy)-3-methoxy-phenyl]-acrylic acid (2R,3S,4S,5R,6R)-6-[2-(4-allyloxy-phenyl)-ethoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl ester 
• 797041-00-0 Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(4-allyloxy-phenyl)-ethoxy]-tetrahydro-pyran-4-yl ester 
• 854261-52-2 allyl (E)-3-(4-(allyloxy)-3-methoxyphenyl)acrylate 
• 190122-90-8 Chloro-acetic acid 4-((E)-2-chlorocarbonyl-vinyl)-2-methoxy-phenyl ester 
• 190122-81-7 (E)-3-[4-(2-Chloro-acetoxy)-3-methoxy-phenyl]-acrylic acid 
• 115375-24-1 (E)-3-(4-(allyloxy)-3-methoxyphenyl)acrylic acid 
• 98704-58-6 2-(4-(allyloxy)phenyl)ethanol 
• 25244-30-8 4-(allyloxy)bromobenzene 

Relevant articles and documents

Short synthesis of phenylpropanoid glycoside grayanoside-A and analogues

A short synthesis of phenylethyl glycosides grayanoside-A 1, 2 and analogues 3–4 in high 43–65% overall yields is described. The main synthetic step involved regioselective O-6 acylation of unprotected 2-phenylethyl-β-D-glucoside 7 with cinnamoyl chlorides 8a-d using Me2SnCl2as catalyst. The acylation at O-6 is regioselective regardless of the type of cinnamoyl chloride used. Protection/deprotection steps of the glucoside core were not necessary. The synthetic route is generally applicable for the synthesis of phenylpropanoid glycoside class of compounds acylated at O-6.

Total synthesis of the phenylpropanoid glycoside, grayanoside A

Grayanoside A, 2-(4-hydroxyphenyl)ethyl 6-O-feruloyl-β-D-glucopyranoside, was synthesized for the first time by using chloroacetyl groups for the protection of hydroxy functions. 2-(4-Allyloxyphenyl)ethyl 4-O-[(4-O-allyl)feruloyl]-2,3,6-tri-O-chloroacetyl-β-D-glucopyranoside (12) was synthesized from 2-(4-allyloxyphenyl)ethyl 4,6-O-benzylidene-β-D-glucopyranoside (8) in four steps with the goal of preparing syringalide B. It was found, however, that the feruloyl group migrated from the 4- to the 6-position of the glycopyranoside during the deprotection of 12.