(2S,3R,4S,5S,6R)-2-[2-hydroxy-4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Base Information

• Chemical Name: (2S,3R,4S,5S,6R)-2-[2-hydroxy-4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS No.: 54695-80-6
• Molecular Formula: C14H20O8
• Molecular Weight: 316.308
• DSSTox Substance ID: DTXSID50969991
• Nikkaji Number: J998.426G
• Wikidata: Q82953068
• Mol file: 54695-80-6.mol

Synonyms:54695-80-6;2-Hydroxy-4-(2-hydroxyethyl)phenyl-beta-D-glucopyranoside;(2S,3R,4S,5S,6R)-2-[2-hydroxy-4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol;beta-D-Glucopyranoside, 2-hydroxy-4-(2-hydroxyethyl)phenyl-;C14-H20-O8;SCHEMBL3300991;DTXSID50969991;CHEBI:181056;Hydroxytyrosol 4-beta-D-glucoside;NCGC00386029-01;2-Hydroxy-4-(2-hydroxyethyl)phenyl hexopyranoside;NCGC00386029-01_C14H20O8_2-Hydroxy-4-(2-hydroxyethyl)phenyl beta-D-glucopyranoside;(2S,3R,4S,5S,6R)-2-[2-hydroxy-4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol

Chemical Property of (2S,3R,4S,5S,6R)-2-[2-hydroxy-4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Chemical Property:

• Vapor Pressure: 6.63E-16mmHg at 25°C
• Boiling Point: 613.5°Cat760mmHg
• Flash Point: 324.8°C
• Density: 1.54g/cm³
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 316.11581759
• Heavy Atom Count: 22
• Complexity: 341

Purity/Quality:

98.0% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1CCO)O)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1CCO)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O

Technology Process of (2S,3R,4S,5S,6R)-2-[2-hydroxy-4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

There total 3 articles about (2S,3R,4S,5S,6R)-2-[2-hydroxy-4-(2-hydroxyethyl)phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

3,4-dihydroxyphenethyl alcohol 4-O-β-D-(6-O-galloyl)-glucopyranoside (115397-25-6) → 3,4,5-trihydroxybenzoic acid (149-91-7) + 3,4-dihydroxyphenethyl alcohol 4-O-β-D-glucopyranoside (54695-80-6)

Guidance literature:

With tannase; for 2h; Ambient temperature; incubation;

Reference yield:

4′-O-[6″-O-(4?-hydroxy-3?,5?-dimethoxybenzoyl)-β-D-glucopyranosyl]-3′-hydroxyphenethylalcohol (1346265-63-1) → 3,4-dihydroxyphenethyl alcohol 4-O-β-D-glucopyranoside (54695-80-6)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃;

DOI:10.1016/j.phytochem.2011.07.008

Reference yield:

hydroxytyrosol (10597-60-1) → 2-(3,4-dihydrophenyl)ethanol-3'-O-β-D-glucopyranoside (142542-89-0) + 2-(3,4-dihydrophenyl)ethanol-4'-O-β-D-glucopyranoside (54695-80-6) + β-(3,4-dihydroxyphenyl)-ethyl-O-β-D-glucopyranoside (76873-99-9)

Guidance literature:

hydroxytyrosol; With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃;

With formic acid; In N,N-dimethyl-formamide;

With hydrogenchloride; sodium methylate; more than 3 stages;

upstream raw materials:

3,4-dihydroxyphenethyl alcohol 4-O-β-D-(6-O-galloyl)-glucopyranoside

4′-O-[6″-O-(4?-hydroxy-3?,5?-dimethoxybenzoyl)-β-D-glucopyranosyl]-3′-hydroxyphenethylalcohol

hydroxytyrosol

Downstream raw materials:

alpha-D-glucopyranose