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

Base Information

Chemical Name:(2R)-5-(benzyloxycarbonylamino)-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-ol benzyloxymethyl ether
CAS No.:346669-95-2
Molecular Formula:C₄₂H₆₀N₂O₆
Molecular Weight:688.948
Hs Code.:

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

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

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

There total 5 articles about (2R)-5-(benzyloxycarbonylamino)-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: 92.0%

: 253586-97-9
(2R)-5-benzyloxycarbonylamino-2-[(R)-3-benzyloxytetradecanoylamino]pentan-1-ol

: 3587-60-8
Benzyloxymethyl chloride

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

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;
DOI:10.1021/jm060482a

Reference yield:

: (R)-3-Trimethylsilanyloxy-tetradecanoic acid methyl ester

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

Guidance literature:: Multi-step reaction with 4 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

With 4-methyl-morpholine; triethylsilane; lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; isobutyl chloroformate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jm060482a

Reference yield:

: 76062-97-0
methyl (R)-3-hydroxytetradecanoate

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

Guidance literature:: Multi-step reaction with 5 steps

1.1: Et₃N / tetrahydrofuran / 17 h / 20 °C

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

3.1: 10.4 g / aq. LiOH / tetrahydrofuran / 6.5 h / Heating

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

4.2: 69 percent / Et₃N / tetrahydrofuran / 16 h / 20 °C

5.1: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 20 °C

With 4-methyl-morpholine; triethylsilane; lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; triethylamine; N-ethyl-N,N-diisopropylamine; isobutyl chloroformate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jm060482a