(4S,5R)-3-((2S,3R)-2-isobutyl-3-hydroxypent-4-enoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-on

Base Information

Chemical Name:(4S,5R)-3-((2S,3R)-2-isobutyl-3-hydroxypent-4-enoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-on
CAS No.:244177-70-6
Molecular Formula:C₁₉H₂₅NO₄
Molecular Weight:331.412
Hs Code.:

Synonyms:(4S,5R)-3-((2S,3R)-2-isobutyl-3-hydroxypent-4-enoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-on

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Chemical Property of (4S,5R)-3-((2S,3R)-2-isobutyl-3-hydroxypent-4-enoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-on

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Technology Process of (4S,5R)-3-((2S,3R)-2-isobutyl-3-hydroxypent-4-enoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-on

There total 7 articles about (4S,5R)-3-((2S,3R)-2-isobutyl-3-hydroxypent-4-enoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-on 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: 70.0%

: 107-02-8,25068-14-8
acrolein

: 168540-62-3
(4S,5R)-3-(4-methylpentanoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-on

: 244177-70-6
(4S,5R)-3-((2S,3R)-2-isobutyl-3-hydroxypent-4-enoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-on

Guidance literature:: (4S,5R)-3-(4-methylpentanoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-on; With titanium tetrachloride; In dichloromethane; at -78 ℃; for 0.25h;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 2h;

acrolein; With 1-methyl-pyrrolidin-2-one; In dichloromethane; at -78 - 0 ℃; for 2h;
DOI:10.1021/ol301612q

Reference yield:

: 16251-45-9,17097-67-5,28044-22-6,28044-23-7,39663-75-7,54418-69-8,77943-39-6,125133-96-2,149055-02-7
(4S,5R)-4-methyl-5-phenyl-oxazolidin-2-one

: 244177-70-6
(4S,5R)-3-((2S,3R)-2-isobutyl-3-hydroxypent-4-enoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-on

Guidance literature:: Multi-step reaction with 2 steps

1.1: 2-chloro-1-methylpyridinium iodide; Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 1.5 h / 23 °C

2.1: di-n-butylboron trifluoromethanesulfonate; i-Pr₂NEt / CH₂Cl₂ / 0.33 h / 0 °C

2.2: CH₂Cl₂ / 0.67 h / -78 - 0 °C

With dmap; di-n-butylboryl trifluoromethanesulfonate; 2-chloro-1-methyl-pyridinium iodide; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1021/ja0023377

Reference yield:

: 107-02-8,25068-14-8
acrolein

: 168540-62-3
(4S,5R)-3-(4-methylpentanoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-on

: 244177-70-6
(4S,5R)-3-((2S,3R)-2-isobutyl-3-hydroxypent-4-enoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-on

: (4S,5R)-3-((2R,3S)-3-Hydroxy-2-isobutyl-pent-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:: (4S,5R)-3-(4-methylpentanoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-on; With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.333333h;

acrolein; In dichloromethane; at -78 - 0 ℃; for 0.666667h; Further stages.;
DOI:10.1021/ja0023377