4-(R)-benzyl-3-{2-(S)-[1-(R)-benzyloxymethyl-allyloxy]-3-(R)-hydroxy-pentadecanoyl}oxazolidin-2-one

Base Information

Chemical Name:4-(R)-benzyl-3-{2-(S)-[1-(R)-benzyloxymethyl-allyloxy]-3-(R)-hydroxy-pentadecanoyl}oxazolidin-2-one
CAS No.:790698-04-3
Molecular Formula:C₃₆H₅₁NO₆
Molecular Weight:593.804
Hs Code.:

Synonyms:4-(R)-benzyl-3-{2-(S)-[1-(R)-benzyloxymethyl-allyloxy]-3-(R)-hydroxy-pentadecanoyl}oxazolidin-2-one

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Chemical Property of 4-(R)-benzyl-3-{2-(S)-[1-(R)-benzyloxymethyl-allyloxy]-3-(R)-hydroxy-pentadecanoyl}oxazolidin-2-one

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Technology Process of 4-(R)-benzyl-3-{2-(S)-[1-(R)-benzyloxymethyl-allyloxy]-3-(R)-hydroxy-pentadecanoyl}oxazolidin-2-one

There total 4 articles about 4-(R)-benzyl-3-{2-(S)-[1-(R)-benzyloxymethyl-allyloxy]-3-(R)-hydroxy-pentadecanoyl}oxazolidin-2-one 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: 74.0%

: 10486-19-8
tridecanal

: 790698-03-2
4-(R)-benzyl-3-{2-[1-(R)-benzyloxymethyl-allyloxy]acetyl}oxazolidin-2-one

: 790698-04-3
4-(R)-benzyl-3-{2-(S)-[1-(R)-benzyloxymethyl-allyloxy]-3-(R)-hydroxy-pentadecanoyl}oxazolidin-2-one

Guidance literature:: With 1-methyl-pyrrolidin-2-one; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - -40 ℃;
DOI:10.1021/ja0455852

Reference yield:

: 93553-66-3,109613-59-4,114819-44-2,113426-94-1
(2R)-1-(benzyloxy)but-3-en-2-ol

: 790698-04-3
4-(R)-benzyl-3-{2-(S)-[1-(R)-benzyloxymethyl-allyloxy]-3-(R)-hydroxy-pentadecanoyl}oxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 1 h / 0 °C

1.2: tetrahydrofuran / 0 - 20 °C

2.1: Et₃N; pivaloyl chloride / diethyl ether / 1 h / 0 °C

2.2: n-BuLi / tetrahydrofuran; hexane; diethyl ether / 2 h / 0 °C

3.1: 74 percent / TiCl₄; i-Pr₂NEt; N-methyl-2-pyrrolidinone / CH₂Cl₂ / -78 - -40 °C

With 1-methyl-pyrrolidin-2-one; pivaloyl chloride; titanium tetrachloride; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja0455852

Reference yield:

: 14618-80-5
(R)-benzyl glycidol

: 790698-04-3
4-(R)-benzyl-3-{2-(S)-[1-(R)-benzyloxymethyl-allyloxy]-3-(R)-hydroxy-pentadecanoyl}oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran / -10 - 25 °C

2.1: NaH / tetrahydrofuran / 1 h / 0 °C

2.2: tetrahydrofuran / 0 - 20 °C

3.1: Et₃N; pivaloyl chloride / diethyl ether / 1 h / 0 °C

3.2: n-BuLi / tetrahydrofuran; hexane; diethyl ether / 2 h / 0 °C

4.1: 74 percent / TiCl₄; i-Pr₂NEt; N-methyl-2-pyrrolidinone / CH₂Cl₂ / -78 - -40 °C

With 1-methyl-pyrrolidin-2-one; n-butyllithium; pivaloyl chloride; titanium tetrachloride; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja0455852