benzyl 4'-(4-O-(methyl 2'',3'',4''-tri-O-acetyl-β-D-glucopyranosyluronate)-2-hydroxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate

Base Information

• Chemical Name: benzyl 4'-(4-O-(methyl 2'',3'',4''-tri-O-acetyl-β-D-glucopyranosyluronate)-2-hydroxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate
• CAS No.: 869996-26-9
• Molecular Formula: C₅₇H₇₀O₁₆
• Molecular Weight: 1011.17
• Mol file: 869996-26-9.mol

Synonyms:benzyl 4'-(4-O-(methyl 2'',3'',4''-tri-O-acetyl-β-D-glucopyranosyluronate)-2-hydroxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate

Chemical Property of benzyl 4'-(4-O-(methyl 2'',3'',4''-tri-O-acetyl-β-D-glucopyranosyluronate)-2-hydroxy-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-(methyl 2'',3'',4''-tri-O-acetyl-β-D-glucopyranosyluronate)-2-hydroxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate

There total 17 articles about benzyl 4'-(4-O-(methyl 2'',3'',4''-tri-O-acetyl-β-D-glucopyranosyluronate)-2-hydroxy-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: 65.0%

benzyl 2-benzyloxy-4-hydroxy-6-methylbenzoate (869996-21-4) + 4-O-(methyl 2',3',4'-tri-O-acetyl-β-D-glucopyranosyluronate)-2-hydroxy-6-pentadecanylbenzoic acid (869996-25-8) → benzyl 4'-(4-O-(methyl 2'',3'',4''-tri-O-acetyl-β-D-glucopyranosyluronate)-2-hydroxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate (869996-26-9)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/jo051384k

Reference yield:

benzyl 2,4-dihydroxy-6-pentadecanylbenzoate (869996-15-6) → benzyl 4'-(4-O-(methyl 2'',3'',4''-tri-O-acetyl-β-D-glucopyranosyluronate)-2-hydroxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate (869996-26-9)

Guidance literature:

Multi-step reaction with 3 steps

1: Ag₂O / acetonitrile / 6 h / 38 °C

2: 89 mg / H₂ / Pd/C / ethyl acetate / 15 h / 20 °C / 760 Torr

3: 65 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; DMAP / CH₂Cl₂ / 4 h / 20 °C

With dmap; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; silver(l) oxide; palladium on activated charcoal; In dichloromethane; ethyl acetate; acetonitrile; 1: Koenigs-Knorr reaction;

DOI:10.1021/jo051384k

Reference yield:

2,4-bis(benzyloxy)-6-pentadecanylbenzoic acid (869996-09-8) → benzyl 4'-(4-O-(methyl 2'',3'',4''-tri-O-acetyl-β-D-glucopyranosyluronate)-2-hydroxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate (869996-26-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / H₂ / Pd/C / ethyl acetate / 5 h / 20 °C / 760 Torr

2: 88 percent / KHCO₃ / dimethylformamide / 40 h / Heating

3: Ag₂O / acetonitrile / 6 h / 38 °C

4: 89 mg / H₂ / Pd/C / ethyl acetate / 15 h / 20 °C / 760 Torr

5: 65 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; DMAP / CH₂Cl₂ / 4 h / 20 °C

With dmap; hydrogen; potassium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; silver(l) oxide; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 3: Koenigs-Knorr reaction;

DOI:10.1021/jo051384k

upstream raw materials:

benzyl 2-benzyloxy-4-hydroxy-6-methylbenzoate

4-O-(methyl 2',3',4'-tri-O-acetyl-β-D-glucopyranosyluronate)-2-hydroxy-6-pentadecanylbenzoic acid

benzyl 2-hydroxy-4-(methoxymethoxy)-6-methylbenzoate

benzyl 2-benzyloxy-4-(methoxymethoxy)-6-methylbenzoate

Downstream raw materials:

benzyl 4'-(4-O-(β-D-glucopyranosyluronic acid)-2-benzyloxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate

benzyl 4'-(4-O-(methyl 2'',3'',4''-tri-O-acetyl-β-D-glucopyranosyluronate)-2-benzyloxy-6-pentadecanylbenzoyloxy)-2'-benzyloxy-6'-methylbenzoate