(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(2-methoxyphenoxy)oxane-3,4,5-triol

Base Information

• Chemical Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(2-methoxyphenoxy)oxane-3,4,5-triol
• CAS No.: 6092-24-6
• Molecular Formula: C13H18O7
• Molecular Weight: 286.282
• DSSTox Substance ID: DTXSID70976389
• Nikkaji Number: J1.268.492D
• Wikidata: Q76009982
• Mol file: 6092-24-6.mol

Synonyms:Guaiacol-beta-glucoside;6092-24-6;Guaiacol beta-glucoside;2-Methoxyphenyl-beta-D-glucopyranoside;(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(2-methoxyphenoxy)oxane-3,4,5-triol;beta-D-Glucopyranoside, 2-methoxyphenyl;beta-D-Glucopyranoside, 2-methoxyphenyl-;2-Methoxyphenyl hexopyranoside;SCHEMBL10307314;DTXSID70976389;guaiacol O-beta-D-glucopyranoside;2-methoxyphenyl beta-d-glucopyranoside;LS-71554

Chemical Property of (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(2-methoxyphenoxy)oxane-3,4,5-triol

Chemical Property:

• Vapor Pressure: 1.12E-10mmHg at 25°C
• Boiling Point: 496.5°Cat760mmHg
• Flash Point: 254.1°C
• Density: 1.427g/cm³
• XLogP3: -1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 286.10525291
• Heavy Atom Count: 20
• Complexity: 300

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC=C1OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: COC1=CC=CC=C1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O

Technology Process of (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(2-methoxyphenoxy)oxane-3,4,5-triol

There total 8 articles about (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(2-methoxyphenoxy)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: 45.0%

2-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (35023-63-3) → o-methoxyphenyl 2-O-acetyl-β-D-glucopyranoside + o-methoxyphenyl 3-O-acetyl-β-D-glucopyranoside + 2-methoxybenzoyl-β-D-glucopyranoside (6092-24-6)

Guidance literature:

With hydrogenchloride; In ethanol; chloroform; water; at 30 ℃; for 12h; regioselective reaction; Kinetics;

DOI:10.1016/j.carres.2018.02.003

Reference yield:

2-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (35023-63-3) → 2-methoxybenzoyl-β-D-glucopyranoside (6092-24-6)

Guidance literature:

With sodium hydroxide;

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2-methoxybenzoyl-β-D-glucopyranoside (6092-24-6)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH solution; acetone

2: sodium methylate; methanol

With methanol; sodium hydroxide; sodium methylate; acetone;

upstream raw materials:

2-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

2-methoxy-phenol

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

D-glucose pentaacetate

Refernces

• 1、 Stepanova, Elena V.,Nagornaya, Marina O.,Filimonov, Victor D.,Valiev, Rashid R.,Belyanin, Maxim L.,Drozdova, Anna K.,Cherepanov, Victor N.. "A new look at acid catalyzed deacetylation of carbohydrates: A regioselective synthesis and reactivity of 2-O-acetyl aryl glycopyranosides". . p. 60 - 66. Retrieved 2018/02/20.