4-methylphenyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidine1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: 4-methylphenyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidine1-thio-β-D-galactopyranoside
• CAS No.: 942044-14-6
• Molecular Formula: C₂₉H₃₀O₆S
• Molecular Weight: 506.62
• Mol file: 942044-14-6.mol

Synonyms:4-methylphenyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidine1-thio-β-D-galactopyranoside

Chemical Property of 4-methylphenyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidine1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-methylphenyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidine1-thio-β-D-galactopyranoside

There total 14 articles about 4-methylphenyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidine1-thio-β-D-galactopyranoside 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: 78.0%

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) + β-naphthaldehyde (66-99-9) + benzoic acid anhydride (93-97-0) → 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) + C33H32O6S (942044-19-1) + 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; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -86 ℃; for 2h; Molecular sieve;

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

acetic anhydride; benzoic acid anhydride; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -86 - 0 ℃; Product distribution / selectivity; Combinatorial reaction / High throughput screening (HTS);

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:

((4aR,6S,7R,8S,8aR)-8-Benzyloxy-2-phenyl-6-p-tolylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-trimethyl-silane + acetic anhydride (108-24-7) → 4-methylphenyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidine1-thio-β-D-galactopyranoside (942044-14-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere; Molecular sieve;

DOI:10.1039/c3ob42097c

upstream raw materials:

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

acetic anhydride

benzaldehyde

4-methoxy-benzaldehyde

Downstream raw materials:

p-tolyl 2-O-acetyl-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside

p-tolyl 2-O-acetyl-3,4-di-O-benzyl-1-thio-β-D-glucopyranoside