O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-N-dodecanoyl-L-serine undecylamide

Base Information

• Chemical Name: O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-N-dodecanoyl-L-serine undecylamide
• CAS No.: 1293922-55-0
• Molecular Formula: C₅₃H₈₀N₂O₈
• Molecular Weight: 873.227

Synonyms:

Chemical Property of O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-N-dodecanoyl-L-serine undecylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-N-dodecanoyl-L-serine undecylamide

There total 7 articles about O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-N-dodecanoyl-L-serine undecylamide 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:

1,6-di-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside (35094-65-6) → O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-N-dodecanoyl-L-serine undecylamide (1293922-55-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: trimethylsilyl iodide / dichloromethane / 0.17 h / 0 °C / Molecular sieve; Inert atmosphere

2.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / toluene / 3 h / 80 °C / Inert atmosphere; Molecular sieve

3.1: 4-methyl-morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 20 °C / Inert atmosphere

5.1: piperidine / dichloromethane / 0.33 h / 20 °C / Inert atmosphere

6.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

7.1: methanol; sodium methylate / Inert atmosphere

With piperidine; 4-methyl-morpholine; methanol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; trimethylsilyl iodide; sodium methylate; tetra-(n-butyl)ammonium iodide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1039/c0ob00990c

Reference yield:

C29H31IO6 → O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-N-dodecanoyl-L-serine undecylamide (1293922-55-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / toluene / 3 h / 80 °C / Inert atmosphere; Molecular sieve

2.1: 4-methyl-morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

2.2: Inert atmosphere

3.1: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 20 °C / Inert atmosphere

4.1: piperidine / dichloromethane / 0.33 h / 20 °C / Inert atmosphere

5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

6.1: methanol; sodium methylate / Inert atmosphere

With piperidine; 4-methyl-morpholine; methanol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium methylate; tetra-(n-butyl)ammonium iodide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1039/c0ob00990c

Reference yield:

N-(9-fluorenylmethoxycarbonyl)-O-(2,3,4-tri-O-benzyl-6-O-acetyl-α-D-glucopyranosyl)-L-serine allyl ester (1293922-54-9) → O-(2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-N-dodecanoyl-L-serine undecylamide (1293922-55-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 4-methyl-morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 20 °C / Inert atmosphere

3.1: piperidine / dichloromethane / 0.33 h / 20 °C / Inert atmosphere

4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

5.1: methanol; sodium methylate / Inert atmosphere

With piperidine; 4-methyl-morpholine; methanol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium methylate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1039/c0ob00990c

upstream raw materials:

1,6-di-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside

N-(9-fluorenylmethoxycarbonyl)-O-(2,3,4-tri-O-benzyl-6-O-acetyl-α-D-glucopyranosyl)-L-serine allyl ester

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