(R)-4-Isopropyl-3-[(S)-2-(4-methoxy-benzyloxy)-pent-4-enoyl]-oxazolidin-2-one

Base Information

Chemical Name:(R)-4-Isopropyl-3-[(S)-2-(4-methoxy-benzyloxy)-pent-4-enoyl]-oxazolidin-2-one
CAS No.:911237-03-1
Molecular Formula:C₁₉H₂₅NO₅
Molecular Weight:347.411
Hs Code.:

Synonyms:(R)-4-Isopropyl-3-[(S)-2-(4-methoxy-benzyloxy)-pent-4-enoyl]-oxazolidin-2-one

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Chemical Property of (R)-4-Isopropyl-3-[(S)-2-(4-methoxy-benzyloxy)-pent-4-enoyl]-oxazolidin-2-one

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Technology Process of (R)-4-Isopropyl-3-[(S)-2-(4-methoxy-benzyloxy)-pent-4-enoyl]-oxazolidin-2-one

There total 1 articles about (R)-4-Isopropyl-3-[(S)-2-(4-methoxy-benzyloxy)-pent-4-enoyl]-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: 76.0%

: 556-56-9
allyl iodid

: (R)-(+)-[4-isopropyl-3-(4-methoxybenzyloxy)acetyl]-2-oxazolidinone

: 911237-03-1
(R)-4-Isopropyl-3-[(S)-2-(4-methoxy-benzyloxy)-pent-4-enoyl]-oxazolidin-2-one

Guidance literature:: (R)-(+)-[4-isopropyl-3-(4-methoxybenzyloxy)acetyl]-2-oxazolidinone; With sodium hexamethyldisilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.75h;

allyl iodid; In tetrahydrofuran; toluene; at -78 - -40 ℃;
DOI:10.1021/ol0615782

Reference yield: 93.0%

: 911237-03-1
(R)-4-Isopropyl-3-[(S)-2-(4-methoxy-benzyloxy)-pent-4-enoyl]-oxazolidin-2-one

: 911237-04-2
(2S)-2-(4-methoxybenzyloxy)-4-pentenol

Guidance literature:: With lithium borohydride; In methanol; diethyl ether; at 0 ℃; for 2h;
DOI:10.1021/ol0615782

Reference yield:

: 911237-03-1
(R)-4-Isopropyl-3-[(S)-2-(4-methoxy-benzyloxy)-pent-4-enoyl]-oxazolidin-2-one

: C₄₁H₅₄O₈

Guidance literature:: Multi-step reaction with 31 steps

1.1: 93 percent / LiBH₄ / diethyl ether; methanol / 2 h / 0 °C

2.1: (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -78 - -65 °C

3.1: TiCl₄; (-)-sparteine; N-methylpyrrolidinone / CH₂Cl₂ / 0 °C

3.2: CH₂Cl₂ / -78 - -30 °C

4.1: 10.3 g / NaBH₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

5.1: 97 percent / imidazole / CH₂Cl₂ / 15 h / 20 °C

6.1: NaH / tetrahydrofuran; dimethylformamide / 0.17 h / 0 °C

6.2: 92 percent / tetrahydrofuran; dimethylformamide / 15 h / 20 °C

7.1: Et₃N / tetrahydrofuran / -78 - 0 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

8.2: 17.0 g / tetrahydrofuran; hexane / -78 - 0 °C

9.1: NaN(SiMe₃)2 / toluene; tetrahydrofuran / 1 h / -78 °C

9.2: toluene; tetrahydrofuran / 1 h / -78 °C

10.1: 11.0 g / NaBH₄ / tetrahydrofuran; H₂O / 2 h / 20 °C

11.1: (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -78 - -65 °C

12.1: AlMe₃ / CH₂Cl₂; toluene / 1 h / -78 °C

13.1: 69 percent / aq. HCl / methanol / 3 h / 65 °C

14.1: 80 percent / imidazole / dimethylformamide / 15 h / 80 °C

15.1: 88 percent / LiAlH₄ / diethyl ether / 0.5 h / -20 °C

16.1: 98 percent / NaH / dimethylformamide / 15 h / 20 °C

17.1: 72 percent / HF*pyridine / tetrahydrofuran / 3 h / 20 °C

18.1: 97 percent / imidazole; Ph₃P; I₂ / benzene / 1 h / 20 °C

19.1: 96 percent / dimethylsulfoxide / 15 h

20.1: 81 percent / i-Bu₂AlH / CH₂Cl₂; hexane / 3 h / 0 °C

21.1: n-BuLi / tetrahydrofuran; hexane / 1.25 h / -78 °C

21.2: 96 percent / tetrahydrofuran; hexane / -78 - 0 °C

22.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 20 °C

23.1: 100 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 4 h / 40 °C

24.1: Ba(OH)2 / tetrahydrofuran / 0.5 h / 20 °C

24.2: 96 percent / tetrahydrofuran; H₂O / 0.5 h / 20 °C

25.1: 92 percent / Me₂PhSiH; (PPh₃)3RhCl / toluene / 50 °C

26.1: dimethyldioxirane / CH₂Cl₂ / -78 °C

26.2: i-Bu₂AlH / CH₂Cl₂; hexane / -78 °C

27.1: 0.080 g / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

28.1: 66 percent / K₂CO₃ / methanol / 65 °C

29.1: 34 percent / camphorsulfonic acid / 3 h / Heating

30.1: 78 percent / Me₂PhSiH; BF₃*OEt₂ / CH₂Cl₂ / 0.25 h / 0 °C

31.1: 63 percent / 4-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 2 h / 0 °C

With 1H-imidazole; 1-methyl-pyrrolidin-2-one; hydrogenchloride; barium dihydroxide; sodium tetrahydroborate; Wilkinson's catalyst; lithium aluminium tetrahydride; Grubbs catalyst first generation; lithium borohydride; n-butyllithium; tetrapropylammonium perruthennate; oxalyl dichloride; Dimethylphenylsilane; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; iodine; trimethylaluminum; sodium hexamethyldisilazane; 3,3-dimethyldioxirane; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; (-)-sparteine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene; 2.1: Swern oxidation / 11.1: Swern oxidation / 12.1: Felkin-Anh allylation;
DOI:10.1021/ol0615782