benzyl 4'-(4-O-(2'',3''-di-O-acetyl-4'',6''-O-benzylidene-β-D-glucopyranosyl)-2-benzyloxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate

Base Information

• Chemical Name: benzyl 4'-(4-O-(2'',3''-di-O-acetyl-4'',6''-O-benzylidene-β-D-glucopyranosyl)-2-benzyloxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate
• CAS No.: 869996-13-4
• Molecular Formula: C₆₈H₇₈O₁₄
• Molecular Weight: 1119.36
• Mol file: 869996-13-4.mol

Synonyms:benzyl 4'-(4-O-(2'',3''-di-O-acetyl-4'',6''-O-benzylidene-β-D-glucopyranosyl)-2-benzyloxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate

Chemical Property of benzyl 4'-(4-O-(2'',3''-di-O-acetyl-4'',6''-O-benzylidene-β-D-glucopyranosyl)-2-benzyloxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 4'-(4-O-(2'',3''-di-O-acetyl-4'',6''-O-benzylidene-β-D-glucopyranosyl)-2-benzyloxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate

There total 15 articles about benzyl 4'-(4-O-(2'',3''-di-O-acetyl-4'',6''-O-benzylidene-β-D-glucopyranosyl)-2-benzyloxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate 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: 80.0%

benzyl 4'-(4-O-(2'',3''-di-O-acetyl-4'',6''-O-benzylidene-β-D-glucopyranosyl)-2-hydroxy-6-pentadecanylbenzoyloxy)-2'-hydroxy-6'-methylbenzoate (869996-12-3) + benzyl bromide (100-39-0) → benzyl 4'-(4-O-(2'',3''-di-O-acetyl-4'',6''-O-benzylidene-β-D-glucopyranosyl)-2-benzyloxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate (869996-13-4)

Guidance literature:

With potassium carbonate; In acetone; for 12h; Heating;

DOI:10.1021/jo051384k

Reference yield:

2,4-bis(benzyloxy)-6-pentadecanylbenzoic acid (869996-09-8) → benzyl 4'-(4-O-(2'',3''-di-O-acetyl-4'',6''-O-benzylidene-β-D-glucopyranosyl)-2-benzyloxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate (869996-13-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / (CF₃CO)2O / toluene / 2 h / 20 °C

2: 100 percent / H₂ / Pd/C / ethyl acetate / 96 h / 20 °C / 760 Torr

3: 89 percent / KHCO₃ / dimethylformamide / 40 h / 20 °C

4: 55 percent / molecular sieves 4 Angstroem; BF₃*OEt₂ / CH₂Cl₂ / 0 - 20 °C

5: 80 percent / K₂CO₃ / acetone / 12 h / Heating

With 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; potassium carbonate; potassium hydrogencarbonate; trifluoroacetic anhydride; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/jo051384k

Reference yield:

2,4-bis-benzyloxy-6-pentadecyl-benzoic acid ethyl ester (869996-08-7) → benzyl 4'-(4-O-(2'',3''-di-O-acetyl-4'',6''-O-benzylidene-β-D-glucopyranosyl)-2-benzyloxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate (869996-13-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.40 g / KOH / dimethylsulfoxide; H₂O / 24 h / 90 °C

2: 94 percent / (CF₃CO)2O / toluene / 2 h / 20 °C

3: 100 percent / H₂ / Pd/C / ethyl acetate / 96 h / 20 °C / 760 Torr

4: 89 percent / KHCO₃ / dimethylformamide / 40 h / 20 °C

5: 55 percent / molecular sieves 4 Angstroem; BF₃*OEt₂ / CH₂Cl₂ / 0 - 20 °C

6: 80 percent / K₂CO₃ / acetone / 12 h / Heating

With potassium hydroxide; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; potassium carbonate; potassium hydrogencarbonate; trifluoroacetic anhydride; palladium on activated charcoal; In dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1021/jo051384k

upstream raw materials:

benzyl 4'-(4-O-(2'',3''-di-O-acetyl-4'',6''-O-benzylidene-β-D-glucopyranosyl)-2-hydroxy-6-pentadecanylbenzoyloxy)-2'-hydroxy-6'-methylbenzoate

benzyl bromide

2,4-bis(benzyloxy)-6-pentadecanylbenzoic acid

2,4-bis-benzyloxy-6-pentadecyl-benzoic acid ethyl ester