797041-00-0

Basic information

• Product Name: Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(4-allyloxy-phenyl)-ethoxy]-tetrahydro-pyran-4-yl ester
• Synonyms: Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(4-allyloxy-phenyl)-ethoxy]-tetrahydro-pyran-4-yl ester
• CAS NO: 797041-00-0
• Molecular Weight: 508.522
• Mol File: 797041-00-0.mol

Chemical Properties

• CAS DataBase Reference: Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(4-allyloxy-phenyl)-ethoxy]-tetrahydro-pyran-4-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(4-allyloxy-phenyl)-ethoxy]-tetrahydro-pyran-4-yl ester(797041-00-0)
• EPA Substance Registry System: Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(4-allyloxy-phenyl)-ethoxy]-tetrahydro-pyran-4-yl ester(797041-00-0)

Safety Data

• Hazardous Substances Data: 797041-00-0(Hazardous Substances Data)

Upstream product

• 98704-58-6 2-(4-(allyloxy)phenyl)ethanol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 106-41-2 4-bromo-phenol 
• 25244-30-8 4-(allyloxy)bromobenzene 
• 14199-15-6 Methyl 4-hydroxyphenylacetate 
• 72224-26-1 methyl 2-(4-(allyloxy)phenyl)acetate 
• 83-87-4 D-glucose pentaacetate 

Downstream Products

• 190122-97-5 [1-(4-allyloxyphenyl)]ethyl β-D-glucopyranoside 
• 145613-78-1 2-(4-hydroxyphenyl)ethyl 6-O-(E)-p-coumaroyl β-D-glucopyranoside 
• 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 
• 190123-17-2 2-(4-allyloxyphenyl)ethyl 2,3-di-O-chloroacetyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 190123-29-6 2-(4-allyloxyphenyl)ethyl 2,3,6-tri-O-chloroacetyl-β-D-glucopyranoside 
• 190123-24-1 2-(4-allyloxyphenyl)ethyl 2,3-di-O-chloroacetyl-β-D-glucopyranoside 
• 190123-12-7 2-(4-allyloxyphenyl)ethyl 4,6-O-benzylidene-β-D-glucopyranoside 
• 110978-95-5 2-(4-hydroxyphenyl)ethyl 6-O-(E)-(3-methoxy-4-hydroxy)cinnamoyl β-D-glucopyranoside 

Relevant articles and documents

Short synthesis of phenylpropanoid glycosides calceolarioside-B and eutigoside-A

A convenient 4-step synthesis of calceolarioside-B 1 and eutigoside-A 2 in high overall yield is described. The key step involved the regioselective, Me2SnCl2-catalyzed O-6 acylation of unprotected 2-phenylethyl-β-D-glucosides 5a–b with cinnamoyl chlorides 6a–b in excellent yields. Acylation at O-6 is selective with the acid chlorides used. This work serves as a model for the convenient synthesis of phenylpropanoid glycosides 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.