p-methylphenyl 4,6-O-benzylidine-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: p-methylphenyl 4,6-O-benzylidine-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside
• CAS No.: 942043-54-1
• Molecular Formula: C₃₁H₃₀O₅S
• Molecular Weight: 514.642
• Mol file: 942043-54-1.mol

Synonyms:p-methylphenyl 4,6-O-benzylidine-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside

Chemical Property of p-methylphenyl 4,6-O-benzylidine-3-O-(naphthalen-2-ylmethyl)-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-benzylidine-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside

There total 5 articles about p-methylphenyl 4,6-O-benzylidine-3-O-(naphthalen-2-ylmethyl)-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: 82.0%

4-methylphenyl 2,3,4,6-tetrakis-O-trimethylsilyl-1-thio-β-D-glucopyranoside (942043-17-6) + pent-3-enal (53448-06-9,58838-14-5,5604-55-7) + benzaldehyde (100-52-7) + 4-methoxy-benzaldehyde (123-11-5) + β-naphthaldehyde (66-99-9) → p-methylphenyl 4,6-O-benzylidine-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside (942043-54-1) + C25H30O5S (1012064-99-1) + para-methylphenyl 4,6-O-benzylidene-3-O-para-methoxybenzyl-1-thio-β-D-glucopyranoside (942043-53-0) + 4-methylphenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

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;

pent-3-enal; benzaldehyde; 4-methoxy-benzaldehyde; β-naphthaldehyde; With triethylsilane; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -86 ℃; for 5h; Combinatorial reaction / High throughput screening (HTS);

With tetrabutyl ammonium fluoride; In dichloromethane; at -86 - 20 ℃;

Reference yield: 65.0%

2-bromomethylnaphthyl bromide (939-26-4) + 4-methylphenyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside (219518-19-1) → p-methylphenyl 4,6-O-benzylidine-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside (942043-54-1)

Guidance literature:

4-methylphenyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside; With di(n-butyl)tin oxide; In toluene; for 3h; Reflux;

2-bromomethylnaphthyl bromide; With cesium fluoride; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jo201586r

Reference yield: 60.0%

4-methylphenyl 2,3,4,6-tetrakis-O-trimethylsilyl-1-thio-β-D-glucopyranoside (942043-17-6) + benzaldehyde (100-52-7) + β-naphthaldehyde (66-99-9) → p-methylphenyl 4,6-O-benzylidine-3-O-(naphthalen-2-ylmethyl)-1-thio-β-D-glucopyranoside (942043-54-1)

Guidance literature:

4-methylphenyl 2,3,4,6-tetrakis-O-trimethylsilyl-1-thio-β-D-glucopyranoside; benzaldehyde; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃;

β-naphthaldehyde; With triethylsilane; In dichloromethane; at -86 ℃;

With tetrabutyl ammonium fluoride; In dichloromethane; at -86 - 20 ℃;

DOI:10.1016/j.tetasy.2009.02.028

upstream raw materials:

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

benzaldehyde

β-naphthaldehyde

pent-3-enal

Downstream raw materials:

p-toluenyl 4,6-O-benzylidene-2-O-levulinoyl-3-O-(2-naphthylmethyl)-L-thio-β-D-glucopyranoside

C₄₅H₄₀O₇S

C₃₉H₃₈O₉S

C₆₀H₆₂O₁₅