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

Base Information

• Chemical Name: (R)-4-Isopropyl-3-[(S)-2-(4-methoxy-benzyloxy)-4-methyl-pent-4-enoyl]-oxazolidin-2-one
• CAS No.: 911236-93-6
• Molecular Formula: C₂₀H₂₇NO₅
• Molecular Weight: 361.438
• Mol file: 911236-93-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (R)-4-Isopropyl-3-[(S)-2-(4-methoxy-benzyloxy)-4-methyl-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: 78.0%

1-iodo-2-methyl-2-propene (3756-30-7) + (R)-(+)-[4-isopropyl-3-(4-methoxybenzyloxy)acetyl]-2-oxazolidinone → (R)-4-Isopropyl-3-[(S)-2-(4-methoxy-benzyloxy)-4-methyl-pent-4-enoyl]-oxazolidin-2-one (911236-93-6)

Guidance literature:

(R)-(+)-[4-isopropyl-3-(4-methoxybenzyloxy)acetyl]-2-oxazolidinone; With sodium hexamethyldisilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

1-iodo-2-methyl-2-propene; In tetrahydrofuran; toluene; at -78 - -45 ℃; for 1.08333h;

DOI:10.1021/ol0615782

Reference yield: 84.0%

(R)-4-Isopropyl-3-[(S)-2-(4-methoxy-benzyloxy)-4-methyl-pent-4-enoyl]-oxazolidin-2-one (911236-93-6) + ethyl acetate (141-78-6) → (S)-4-(4-Methoxy-benzyloxy)-6-methyl-3-oxo-hept-6-enoic acid ethyl ester (911236-70-9)

Guidance literature:

ethyl acetate; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

(R)-4-Isopropyl-3-[(S)-2-(4-methoxy-benzyloxy)-4-methyl-pent-4-enoyl]-oxazolidin-2-one; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

DOI:10.1021/ol0615782

Reference yield:

(R)-4-Isopropyl-3-[(S)-2-(4-methoxy-benzyloxy)-4-methyl-pent-4-enoyl]-oxazolidin-2-one (911236-93-6) → C41H58O8 (911236-91-4)

Guidance literature:

Multi-step reaction with 25 steps

1.1: diisopropylamine; n-BuLi / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 84 percent / tetrahydrofuran; hexane / 1 h / -78 °C

2.1: 80 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

3.1: 100 percent / imidazole / CH₂Cl₂

4.1: 100 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -78 °C

5.1: 79 percent / Zn(BH₄)2 / diethyl ether / -40 - -25 °C

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

6.2: 90 percent / dimethylformamide; tetrahydrofuran / 0 - 20 °C

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

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

8.2: 27.6 g / tetrahydrofuran; hexane / 1.75 h / -78 - 0 °C

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

9.2: 83 percent / tetrahydrofuran; toluene / 1 h / -78 °C

10.1: 86 percent / LiBH₄ / methanol; diethyl ether / 1 h / 0 °C

11.1: 99 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -78 °C

12.1: Mg; I₂ / tetrahydrofuran / 0.5 h

12.2: 86 percent / tetrahydrofuran / 0.08 h / 0 °C

13.1: 52 percent / Cl₂(PCy₃)(Imes)Ru=CHPh / CH₂Cl₂ / Heating

14.1: 94 percent / [PCy₃][COD][Pyr]Ir⁽¹⁺⁾*PF₆^(1-); H₂ / CH₂Cl₂ / -50 °C

15.1: 95 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -78 °C

16.1: 88 percent / tetrahydrofuran; diethyl ether / 0.33 h / -78 °C

17.1: 95 percent / H₂ / Raney nickel / ethanol; H₂O

18.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

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

19.2: 96 percent / tetrahydrofuran; H₂O / 0.5 h / 20 °C

20.1: 92 percent / Me₂PhSiH; (PPh₃)3RhCl / toluene / 50 °C

21.1: dimethyldioxirane / CH₂Cl₂ / -78 °C

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

22.1: 0.080 g / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

23.1: 66 percent / K₂CO₃ / methanol / 65 °C

24.1: 34 percent / camphorsulfonic acid / 3 h / Heating

25.1: 78 percent / Me₂PhSiH; BF₃*OEt₂ / CH₂Cl₂ / 0.25 h / 0 °C

With 1H-imidazole; barium dihydroxide; Wilkinson's catalyst; lithium aluminium tetrahydride; lithium borohydride; Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; n-butyllithium; zinc(II) tetrahydroborate; oxalyl dichloride; (η4-1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) hexafluorophosphate; Dimethylphenylsilane; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; hydrogen; iodine; sodium hexamethyldisilazane; 3,3-dimethyldioxirane; sodium hydride; potassium carbonate; Dess-Martin periodane; magnesium; dimethyl sulfoxide; triethylamine; diisopropylamine; nickel; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.2: Claisen condensation / 4.1: Swern oxidation / 11.1: Swern oxidation / 15.1: Swern oxidation;

DOI:10.1021/ol0615782

upstream raw materials:

1-iodo-2-methyl-2-propene

Downstream raw materials:

(S)-4-(4-Methoxy-benzyloxy)-6-methyl-3-oxo-hept-6-enoic acid ethyl ester

(S)-4-(4-Methoxy-benzyloxy)-6-methyl-hept-6-ene-1,3-diol

(3R,4S)-4-(4-Methoxy-benzyloxy)-6-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol

(S)-4-(4-Methoxy-benzyloxy)-6-methyl-1-triisopropylsilanyloxy-hept-6-en-3-ol