p-methylphenyl 4,6-O-benzylidene-2-O-benzoyl-3-O-(p-methoxybenzyl)-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: p-methylphenyl 4,6-O-benzylidene-2-O-benzoyl-3-O-(p-methoxybenzyl)-1-thio-β-D-glucopyranoside
• CAS No.: 942044-16-8
• Molecular Formula: C₃₅H₃₄O₇S
• Molecular Weight: 598.717
• Mol file: 942044-16-8.mol

Synonyms:p-methylphenyl 4,6-O-benzylidene-2-O-benzoyl-3-O-(p-methoxybenzyl)-1-thio-β-D-glucopyranoside

Chemical Property of p-methylphenyl 4,6-O-benzylidene-2-O-benzoyl-3-O-(p-methoxybenzyl)-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-methylphenyl 4,6-O-benzylidene-2-O-benzoyl-3-O-(p-methoxybenzyl)-1-thio-β-D-glucopyranoside

There total 16 articles about p-methylphenyl 4,6-O-benzylidene-2-O-benzoyl-3-O-(p-methoxybenzyl)-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: 94.0%

para-methylphenyl 4,6-O-benzylidene-3-O-para-methoxybenzyl-1-thio-β-D-glucopyranoside (942043-53-0) + benzoic acid anhydride (93-97-0) → p-methylphenyl 4,6-O-benzylidene-2-O-benzoyl-3-O-(p-methoxybenzyl)-1-thio-β-D-glucopyranoside (942044-16-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1039/c9ob00057g

Reference yield: 75.0%

4-methylphenyl 2,3,4,6-tetrakis-O-trimethylsilyl-1-thio-β-D-glucopyranoside (942043-17-6) + acetic anhydride (108-24-7) + benzaldehyde (100-52-7) + 4-methoxy-benzaldehyde (123-11-5) + benzoyl chloride (98-88-4) + β-naphthaldehyde (66-99-9) → 4-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-benzyl-1-thio-β-D-glucopyranoside (942043-30-3) + 4-methylphenyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidine1-thio-β-D-galactopyranoside (942044-14-6) + C30H32O7S (942044-15-7) + C33H32O6S (942044-19-1) + p-methylphenyl 4,6-O-benzylidene-2-O-benzoyl-3-O-(p-methoxybenzyl)-1-thio-β-D-glucopyranoside (942044-16-8) + p-tolyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(naphthalene-2-ylmethyl)-1-thio-β-D-glucopyranoside (942044-20-4)

Guidance literature:

4-methylphenyl 2,3,4,6-tetrakis-O-trimethylsilyl-1-thio-β-D-glucopyranoside; benzaldehyde; β-naphthaldehyde; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -86 ℃; for 2h; Molecular sieve; Combinatorial reaction / High throughput screening (HTS);

benzaldehyde; 4-methoxy-benzaldehyde; β-naphthaldehyde; With triethylsilane; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -86 ℃; for 5h; Combinatorial reaction / High throughput screening (HTS);

acetic anhydride; benzoyl chloride; With tetrabutyl ammonium fluoride; triethylamine; more than 3 stages; Product distribution / selectivity;

Reference yield: 60.0%

4,6-O-benzylidene-2-O-benzoyl-3-O-(p-methoxybenzyl)-1-thio-β-D-glucopyranosyl trichloroacetimidate + para-thiocresol (106-45-6) → p-methylphenyl 4,6-O-benzylidene-2-O-benzoyl-3-O-(p-methoxybenzyl)-1-thio-β-D-glucopyranoside (942044-16-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 1h; stereoselective reaction; Molecular sieve;

DOI:10.1002/ejoc.201403296

upstream raw materials:

4-methylphenyl 2,3,4,6-tetrakis-O-trimethylsilyl-1-thio-β-D-glucopyranoside

acetic anhydride

benzaldehyde

4-methoxy-benzaldehyde