4-Methoxyphenyl 3-O-Benzyl-4,6-O-benzylidene-beta-D-glucopyranoside

Base Information

• Chemical Name: 4-Methoxyphenyl 3-O-Benzyl-4,6-O-benzylidene-beta-D-glucopyranoside
• CAS No.: 303127-81-3
• Molecular Formula: C27H28 O7
• Molecular Weight: 464.515
• DSSTox Substance ID: DTXSID10441283
• Wikidata: Q82257995
• Mol file: 303127-81-3.mol

Synonyms:303127-81-3;4-Methoxyphenyl 3-O-Benzyl-4,6-O-benzylidene-beta-D-glucopyranoside;M1640;(2R,4aR,6S,7R,8R,8aR)-6-(4-methoxyphenoxy)-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-ol;DTXSID10441283;CS-0226016;4-Methoxyphenyl 3-O-Benzyl-4,6-O-benzylidene-|A-D-glucopyranoside

Chemical Property of 4-Methoxyphenyl 3-O-Benzyl-4,6-O-benzylidene-beta-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.625
• Boiling Point: 641.98°C at 760 mmHg
• PKA: 12.50±0.70(Predicted)
• Flash Point: 342.057°C
• PSA: 75.61000
• Density: 1.307g/cm³
• LogP: 3.85940
• Storage Temp.: Freezer
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 464.18350323
• Heavy Atom Count: 34
• Complexity: 598

Purity/Quality:

98% ^*data from raw suppliers

4-Methoxyphenyl 3-O-Benzyl-4,6-O-benzylidene-β-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)OC2C(C(C3C(O2)COC(O3)C4=CC=CC=C4)OCC5=CC=CC=C5)O
• Isomeric SMILES: COC1=CC=C(C=C1)O[C@H]2[C@@H]([C@H]([C@H]3[C@H](O2)CO[C@H](O3)C4=CC=CC=C4)OCC5=CC=CC=C5)O

Technology Process of 4-Methoxyphenyl 3-O-Benzyl-4,6-O-benzylidene-beta-D-glucopyranoside

There total 18 articles about 4-Methoxyphenyl 3-O-Benzyl-4,6-O-benzylidene-beta-D-glucopyranoside 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: 84.0%

benzaldehyde (100-52-7) + 4-Methoxyphenyl 3-O-benzyl-β-D-glucopyranoside (303127-80-2) → p-methoxyphenyl 3-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside (303127-81-3)

Guidance literature:

With trifluoroacetic acid; for 0.333333h;

DOI:10.1039/b002835p

Reference yield: 80.0%

benzaldehyde dimethyl acetal (1125-88-8) + C19H22O7 → p-methoxyphenyl 3-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside (303127-81-3)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; at 25 ℃; Inert atmosphere;

DOI:10.1002/chem.202000496

Reference yield: 73.0%

benzyl bromide (100-39-0) + 4-methoxyphenyl 4,6-di-O-benzylidene-β-D-glucopyranoside → p-methoxyphenyl 3-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside (303127-81-3)

Guidance literature:

4-methoxyphenyl 4,6-di-O-benzylidene-β-D-glucopyranoside; With di(n-butyl)tin oxide; In methanol; for 3h; Reflux;

benzyl bromide; With cesium fluoride; In N,N-dimethyl-formamide; at 80 ℃; for 6h; regioselective reaction;

DOI:10.1016/j.carres.2011.08.004

upstream raw materials:

benzaldehyde

4-Methoxyphenyl 3-O-benzyl-β-D-glucopyranoside

benzaldehyde dimethyl acetal

4-Methoxyphenyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranoside

Downstream raw materials:

4-Methoxyphenyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

p-methoxypheyl 3-O-benzyl-4,6-O-benzylidene-2-O-trifluoroethylsulfonato-β-D-glucopyranoside

p-methoxyphenyl 3-O-benzyl-4,6-di-O-benzylidene-2-O-pivaloyl-β-D-glucopyranoside

tert-butyldimethylsilyl 3-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside