N-[(R)-3-dodecanoyloxytetradecanoyl]-L-homoserine α-N-{(4R)-5-(benzyloxymethoxy)-4-[(R)-3-benzyloxytetradecanoylamino]pentyl}amide

Base Information

• Chemical Name: N-[(R)-3-dodecanoyloxytetradecanoyl]-L-homoserine α-N-{(4R)-5-(benzyloxymethoxy)-4-[(R)-3-benzyloxytetradecanoylamino]pentyl}amide
• CAS No.: 346670-00-6
• Molecular Formula: C₆₄H₁₀₉N₃O₉
• Molecular Weight: 1064.58
• Mol file: 346670-00-6.mol

Synonyms:N-[(R)-3-dodecanoyloxytetradecanoyl]-L-homoserine α-N-{(4R)-5-(benzyloxymethoxy)-4-[(R)-3-benzyloxytetradecanoylamino]pentyl}amide

Chemical Property of N-[(R)-3-dodecanoyloxytetradecanoyl]-L-homoserine α-N-{(4R)-5-(benzyloxymethoxy)-4-[(R)-3-benzyloxytetradecanoylamino]pentyl}amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(R)-3-dodecanoyloxytetradecanoyl]-L-homoserine α-N-{(4R)-5-(benzyloxymethoxy)-4-[(R)-3-benzyloxytetradecanoylamino]pentyl}amide

There total 17 articles about N-[(R)-3-dodecanoyloxytetradecanoyl]-L-homoserine α-N-{(4R)-5-(benzyloxymethoxy)-4-[(R)-3-benzyloxytetradecanoylamino]pentyl}amide 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:

Benzyloxymethyl chloride (3587-60-8) → N-[(R)-3-dodecanoyloxytetradecanoyl]-L-homoserine α-N-{(4R)-5-(benzyloxymethoxy)-4-[(R)-3-benzyloxytetradecanoylamino]pentyl}amide (346670-00-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 20 °C

2.1: 98 percent / Et₃N; H₂ / Pd(OH)2/C / ethanol / 3 h / 20 °C / atmospheric pressure

3.1: 2-isobutyloxy-1-isobutyloxycarbonyl-1,2-dihydroquinoline / CH₂Cl₂ / 3 h / 20 °C

4.1: Et₃N; H₂ / Pd/C / ethanol; ethyl acetate / 1 h / 20 °C / atmospheric pressure

5.1: N-methylmorpholine; isobutyl chloroformate / tetrahydrofuran / 0.5 h / 20 °C

5.2: NaBH₄ / tetrahydrofuran / 0.08 h / 20 °C

With 4-methyl-morpholine; 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; isobutyl chloroformate; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate;

DOI:10.1021/jm060482a

Reference yield:

(2R)-5-amino-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-ol benzyloxymethyl ether (346669-96-3) → N-[(R)-3-dodecanoyloxytetradecanoyl]-L-homoserine α-N-{(4R)-5-(benzyloxymethoxy)-4-[(R)-3-benzyloxytetradecanoylamino]pentyl}amide (346670-00-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 2-isobutyloxy-1-isobutyloxycarbonyl-1,2-dihydroquinoline / CH₂Cl₂ / 3 h / 20 °C

2.1: Et₃N; H₂ / Pd/C / ethanol; ethyl acetate / 1 h / 20 °C / atmospheric pressure

3.1: N-methylmorpholine; isobutyl chloroformate / tetrahydrofuran / 0.5 h / 20 °C

3.2: NaBH₄ / tetrahydrofuran / 0.08 h / 20 °C

With 4-methyl-morpholine; 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline; hydrogen; triethylamine; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate;

DOI:10.1021/jm060482a

Reference yield:

(R)-3-Trimethylsilanyloxy-tetradecanoic acid methyl ester → N-[(R)-3-dodecanoyloxytetradecanoyl]-L-homoserine α-N-{(4R)-5-(benzyloxymethoxy)-4-[(R)-3-benzyloxytetradecanoylamino]pentyl}amide (346670-00-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: trimethylsilyl triflate; triethylsilane / CH₂Cl₂ / 14 h / 20 °C

2.1: 10.4 g / aq. LiOH / tetrahydrofuran / 6.5 h / Heating

3.1: N-methylmorpholine; isobutyl chloroformate / tetrahydrofuran / 0.5 h / -15 °C

3.2: 69 percent / Et₃N / tetrahydrofuran / 16 h / 20 °C

4.1: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 20 °C

5.1: 98 percent / Et₃N; H₂ / Pd(OH)2/C / ethanol / 3 h / 20 °C / atmospheric pressure

6.1: 2-isobutyloxy-1-isobutyloxycarbonyl-1,2-dihydroquinoline / CH₂Cl₂ / 3 h / 20 °C

7.1: Et₃N; H₂ / Pd/C / ethanol; ethyl acetate / 1 h / 20 °C / atmospheric pressure

8.1: N-methylmorpholine; isobutyl chloroformate / tetrahydrofuran / 0.5 h / 20 °C

8.2: NaBH₄ / tetrahydrofuran / 0.08 h / 20 °C

With 4-methyl-morpholine; triethylsilane; lithium hydroxide; 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline; trimethylsilyl trifluoromethanesulfonate; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; isobutyl chloroformate; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate;

DOI:10.1021/jm060482a

upstream raw materials:

benzyl (R)-3-dodecanoyloxytetradecanoate

(2R)-5-amino-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-ol benzyloxymethyl ether

(2R)-5-benzyloxycarbonylamino-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-ol

(2R)-5-(benzyloxycarbonylamino)-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-ol benzyloxymethyl ether