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

Base Information

• Chemical Name: (2R)-5-amino-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-ol benzyloxymethyl ether
• CAS No.: 346669-96-3
• Molecular Formula: C₃₄H₅₄N₂O₄
• Molecular Weight: 554.814
• Mol file: 346669-96-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (2R)-5-amino-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-ol benzyloxymethyl ether 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: 98.0%

(2R)-5-(benzyloxycarbonylamino)-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-ol benzyloxymethyl ether (346669-95-2) → (2R)-5-amino-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-ol benzyloxymethyl ether (346669-96-3)

Guidance literature:

With hydrogen; triethylamine; palladium dihydroxide; In ethanol; at 20 ℃; for 3h; atmospheric pressure;

DOI:10.1021/jm060482a

Reference yield:

(R)-3-Trimethylsilanyloxy-tetradecanoic acid methyl ester → (2R)-5-amino-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-ol benzyloxymethyl ether (346669-96-3)

Guidance literature:

Multi-step reaction with 5 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

With 4-methyl-morpholine; triethylsilane; lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; isobutyl chloroformate; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/jm060482a

Reference yield:

(2R)-5-benzyloxycarbonylamino-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-ol (253586-97-9) → (2R)-5-amino-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-ol benzyloxymethyl ether (346669-96-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 20 °C

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

With hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In ethanol; dichloromethane;

DOI:10.1021/jm060482a

upstream raw materials:

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

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

Benzyloxymethyl chloride

methyl (R)-3-hydroxytetradecanoate

Downstream raw materials:

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

N-[(R)-3-dodecanoyloxytetradecanoyl]-L-aspartic acid α-N-{(4R)-5-(benzyloxymethoxy)-4-[(R)-3-benzyloxytetradecanoylamino]pentyl}amide β-benzyl ester