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

Base Information

• Chemical Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-methylphenoxy)oxane-3,4,5-triol
• CAS No.: 20274-94-6
• Molecular Formula: C13H18O6
• Molecular Weight: 270.282
• Hs Code.: 2932999099
• DSSTox Substance ID: DTXSID40942394
• Nikkaji Number: J1.605.785A
• Wikidata: Q76006094
• Mol file: 20274-94-6.mol

Synonyms:p-Tolyl-beta-glucoside;20274-94-6;4-Methylphenyl beta-D-glucopyranoside;4-Methylphenyl-beta-D-glucopyranoside;Glucopyranoside, 1-p-tolyl-, beta-D-;beta-D-Glucopyranoside, 4-methylphenyl-;.beta.-D-glucopyranoside, 4-methylphenyl;(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-methylphenoxy)oxane-3,4,5-triol;4-Methylphenyl hexopyranoside;SCHEMBL5027843;DTXSID40942394;LS-71573;(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-methylphenoxy)tetrahydropyran-3,4,5-triol

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

Chemical Property:

• Vapor Pressure: 1.46E-10mmHg at 25°C
• Boiling Point: 493.7°Cat760mmHg
• Flash Point: 252.4°C
• PSA: 99.38000
• Density: 1.401g/cm³
• LogP: -0.82630
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 270.11033829
• Heavy Atom Count: 19
• Complexity: 278

Purity/Quality:

97% ^*data from raw suppliers

4-METHYLPHENYL-BETA-D-GLUCOPYRANOSIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)OC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: CC1=CC=C(C=C1)O[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-(4-methylphenoxy)oxane-3,4,5-triol

There total 16 articles about (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-methylphenoxy)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: 57.0%

4-methylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (14581-78-3) → (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-p-tolyloxy-tetrahydro-pyran-3,4,5-triol (20274-94-6)

Guidance literature:

With sodium carbonate; In methanol; at 20 ℃; for 5h;

DOI:10.1055/s-2003-42048

Reference yield: 49.0%

Acetic acid (3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-p-tolyloxy-tetrahydro-pyran-3-yl ester → 4-methylphenyl α-D-glucopyranoside (3150-22-9,19887-84-4,20274-94-6,25320-78-9,28541-74-4,34246-17-8,89824-78-2)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1039/P19950000027

Reference yield: 25.0%

4-methylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (14581-78-3) → (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-p-tolyloxy-tetrahydro-pyran-3,4,5-triol (20274-94-6) + C15H20O7 + p-cresyl 2-O-acetyl-β-D-glucopyranoside

Guidance literature:

With hydrogenchloride; In ethanol; chloroform; water; at 30 ℃; for 10h; regioselective reaction; Kinetics;

DOI:10.1016/j.carres.2018.02.003

upstream raw materials:

4-methylphenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

β-D-glucose pentaacetate

p-cresol

D-maltose

Downstream raw materials:

4-methylphenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

p-cresolate

(2R,3R,4S,5R,6S)-3,4,5-Trimethoxy-2-methoxymethyl-6-p-tolyloxy-tetrahydro-pyran

(2R,3R,4S,5R,6S)-3,4,5-Trimethoxy-2-methoxymethyl-6-(4-methyl-cyclohexa-1,4-dienyloxy)-tetrahydro-pyran