N-tetradecanoyl-O-<3,4,6-tri-O-acetyl-2-deoxy-2-<(R)-3-tetradecanoyloxytetradecanoylamino>-β-D-glucopyranosyl>-L-seryl-β-alanine benzyl ester

Base Information

• Chemical Name: N-tetradecanoyl-O-<3,4,6-tri-O-acetyl-2-deoxy-2-<(R)-3-tetradecanoyloxytetradecanoylamino>-β-D-glucopyranosyl>-L-seryl-β-alanine benzyl ester
• CAS No.: 197663-31-3
• Molecular Formula: C₆₇H₁₁₃N₃O₁₅
• Molecular Weight: 1200.65
• Mol file: 197663-31-3.mol

Synonyms:N-tetradecanoyl-O-<3,4,6-tri-O-acetyl-2-deoxy-2-<(R)-3-tetradecanoyloxytetradecanoylamino>-β-D-glucopyranosyl>-L-seryl-β-alanine benzyl ester

Chemical Property of N-tetradecanoyl-O-<3,4,6-tri-O-acetyl-2-deoxy-2-<(R)-3-tetradecanoyloxytetradecanoylamino>-β-D-glucopyranosyl>-L-seryl-β-alanine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-tetradecanoyl-O-<3,4,6-tri-O-acetyl-2-deoxy-2-<(R)-3-tetradecanoyloxytetradecanoylamino>-β-D-glucopyranosyl>-L-seryl-β-alanine benzyl ester

There total 4 articles about N-tetradecanoyl-O-<3,4,6-tri-O-acetyl-2-deoxy-2-<(R)-3-tetradecanoyloxytetradecanoylamino>-β-D-glucopyranosyl>-L-seryl-β-alanine benzyl ester 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: 75.0%

β-alanine benzyl ester p-toluenesulfonate (27019-47-2) + N-tetradecanoyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-[(R)-3-tetradecanoyloxytetradecanoylamino]-β-D-glucopyranosyl]-L-serine (186753-98-0) → N-tetradecanoyl-O-<3,4,6-tri-O-acetyl-2-deoxy-2-<(R)-3-tetradecanoyloxytetradecanoylamino>-β-D-glucopyranosyl>-L-seryl-β-alanine benzyl ester (197663-31-3)

Guidance literature:

With 4-methyl-morpholine; WSC*HCl; benzotriazol-1-ol; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 21h;

DOI:10.1248/cpb.48.32

Reference yield:

(R)-3-(dodecanoyloxy)tetradecanoic acid (87357-76-4) → N-tetradecanoyl-O-<3,4,6-tri-O-acetyl-2-deoxy-2-<(R)-3-tetradecanoyloxytetradecanoylamino>-β-D-glucopyranosyl>-L-seryl-β-alanine benzyl ester (197663-31-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 254 mg / DCC; HOBt; N-methylmorpholine / CH₂Cl₂; tetrahydrofuran / 0 - 20 °C

2: 79 percent / H₂ / Pd / tetrahydrofuran; methanol / 20 °C

3: 75 percent / WSC*HCl; N-methylmorpholine; HOBt / dimethylformamide / 21 h / 0 - 20 °C

With 4-methyl-morpholine; WSC*HCl; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: Hydrogenolysis / 3: Acylation;

DOI:10.1248/cpb.48.32

Reference yield:

N-tetradecanoyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-[(R)-3-tetradecanoyloxytetradecanoylamino]-β-D-glucopyranosyl]-L-serine benzyl ester (186754-01-8) → N-tetradecanoyl-O-<3,4,6-tri-O-acetyl-2-deoxy-2-<(R)-3-tetradecanoyloxytetradecanoylamino>-β-D-glucopyranosyl>-L-seryl-β-alanine benzyl ester (197663-31-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / H₂ / Pd / tetrahydrofuran; methanol / 20 °C

2: 75 percent / WSC*HCl; N-methylmorpholine; HOBt / dimethylformamide / 21 h / 0 - 20 °C

With 4-methyl-morpholine; WSC*HCl; hydrogen; benzotriazol-1-ol; palladium; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1: Hydrogenolysis / 2: Acylation;

DOI:10.1248/cpb.48.32

upstream raw materials:

β-alanine benzyl ester p-toluenesulfonate

N-tetradecanoyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-[(R)-3-tetradecanoyloxytetradecanoylamino]-β-D-glucopyranosyl]-L-serine

(R)-3-(dodecanoyloxy)tetradecanoic acid

N-tetradecanoyl-O-[3,4,6-tri-O-acetyl-2-deoxy-2-[(R)-3-tetradecanoyloxytetradecanoylamino]-β-D-glucopyranosyl]-L-serine benzyl ester

Downstream raw materials:

N-tetradecanoyl-O-<2-deoxy-2-<(R)-3-tetradecanoyloxytetradecanoylamino>-β-D-glucopyranosyl>-L-seryl-β-alanine