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

Base Information

Chemical Name:(4S,5R)-3-((2S,3R)-3-Hydroxy-2-methyl-pent-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one
CAS No.:329796-41-0
Molecular Formula:C₁₆H₁₉NO₄
Molecular Weight:289.331
Hs Code.:

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

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Chemical Property of (4S,5R)-3-((2S,3R)-3-Hydroxy-2-methyl-pent-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

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Technology Process of (4S,5R)-3-((2S,3R)-3-Hydroxy-2-methyl-pent-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

There total 2 articles about (4S,5R)-3-((2S,3R)-3-Hydroxy-2-methyl-pent-4-enoyl)-4-methyl-5-phenyl-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:

: 77877-20-4,116382-72-0,143654-01-7
(4S,5R)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one

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

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

: 329796-41-0
(4S,5R)-3-((2S,3R)-3-Hydroxy-2-methyl-pent-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:: (4S,5R)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one; 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

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

: 329796-41-0
(4S,5R)-3-((2S,3R)-3-Hydroxy-2-methyl-pent-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

1.2: tetrahydrofuran; hexane / 0.5 h / -78 - 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 n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ja0023377

Reference yield:

: 329796-41-0
(4S,5R)-3-((2S,3R)-3-Hydroxy-2-methyl-pent-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

: N-[(S)-1-((R)-2-Hydroxy-1-methyl-ethyl)-allyloxy]-4-nitro-benzenesulfonamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: LiBH₄ / diethyl ether; tetrahydrofuran / 0.08 h / 0 °C

2.1: Et₃N / CH₂Cl₂ / 8 h / 23 °C

3.1: triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran / 0.75 h / 23 °C

4.1: MeNH₂ / ethanol; CH₂Cl₂ / 0.25 h / 23 °C

4.2: 2,4,6-collidine / CH₂Cl₂ / 0.25 h / 0 °C

5.1: HF-pyridine / tetrahydrofuran / 10 h / 23 °C

With lithium borohydride; pyridine hydrogenfluoride; triethylamine; triphenylphosphine; methylamine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;
DOI:10.1021/ja0023377