4-methylphenyl-3-O-acetyl-4,6-O-benzylidene-2-deoxyl-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: 4-methylphenyl-3-O-acetyl-4,6-O-benzylidene-2-deoxyl-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 1194397-60-8
• Molecular Formula: C₃₀H₂₇NO₇S
• Molecular Weight: 545.613
• Mol file: 1194397-60-8.mol

Synonyms:4-methylphenyl-3-O-acetyl-4,6-O-benzylidene-2-deoxyl-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property of 4-methylphenyl-3-O-acetyl-4,6-O-benzylidene-2-deoxyl-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-methylphenyl-3-O-acetyl-4,6-O-benzylidene-2-deoxyl-2-phthalimido-1-thio-β-D-glucopyranoside

There total 2 articles about 4-methylphenyl-3-O-acetyl-4,6-O-benzylidene-2-deoxyl-2-phthalimido-1-thio-β-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: 83.0%

C30H45NO6SSi3 + acetic anhydride (108-24-7) + benzaldehyde (100-52-7) → 4-methylphenyl-3-O-acetyl-4,6-O-benzylidene-2-deoxyl-2-phthalimido-1-thio-β-D-glucopyranoside (1194397-60-8)

Guidance literature:

C₃₀H₄₅NO₆SSi₃; benzaldehyde; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 2h; Inert atmosphere; Molecular sieve;

acetic anhydride; In dichloromethane; Inert atmosphere; Molecular sieve;

DOI:10.1002/ejoc.202000923

Reference yield: 78.0%

acetic anhydride (108-24-7) + 4-methylphenyl 4,6-O-benzylidene-2-deoxyl-1-thio-2-phthalimido-β-D-glucopyranoside (220645-16-9) → 4-methylphenyl-3-O-acetyl-4,6-O-benzylidene-2-deoxyl-2-phthalimido-1-thio-β-D-glucopyranoside (1194397-60-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1039/b907351e

Reference yield: 89.0%

4-methylphenyl-3-O-acetyl-4,6-O-benzylidene-2-deoxyl-2-phthalimido-1-thio-β-D-glucopyranoside (1194397-60-8) → p-tolyl 3-O-acetyl-4-O-benzyl-2-deoxy-2-phthalimido-thio-α-D-gluco-pyranoside (1268687-76-8)

Guidance literature:

4-methylphenyl-3-O-acetyl-4,6-O-benzylidene-2-deoxyl-2-phthalimido-1-thio-β-D-glucopyranoside; With sodium tetrahydroborate; In acetonitrile; at 0 ℃; for 0.0833333h;

With 1,3,5-trichloro-2,4,6-triazine; In acetonitrile; for 8h; regioselective reaction;

DOI:10.1016/j.carres.2013.09.003

upstream raw materials:

acetic anhydride

4-methylphenyl 4,6-O-benzylidene-2-deoxyl-1-thio-2-phthalimido-β-D-glucopyranoside

benzaldehyde

Downstream raw materials:

2-azidoethyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→6)-3-O-acetyl-4-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

p-tolyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->6)-3-O-acetyl-4-O-benzyl-2-deoxy-2-phthalimido-thio-β-D-glucopyranoside

p-tolyl 3-O-acetyl-4-O-benzyl-2-deoxy-2-phthalimido-thio-α-D-gluco-pyranoside