(4S)-4-benzyl-3-[(2R,4E)-6-(benzyloxy)-2-methylhex-4-enoyl]-1,3-oxazolidin-2-one

Base Information

• Chemical Name: (4S)-4-benzyl-3-[(2R,4E)-6-(benzyloxy)-2-methylhex-4-enoyl]-1,3-oxazolidin-2-one
• CAS No.: 1000050-92-9
• Molecular Formula: C₂₄H₂₇NO₄
• Molecular Weight: 393.483
• Mol file: 1000050-92-9.mol

Synonyms:(4S)-4-benzyl-3-[(2R,4E)-6-(benzyloxy)-2-methylhex-4-enoyl]-1,3-oxazolidin-2-one

Chemical Property of (4S)-4-benzyl-3-[(2R,4E)-6-(benzyloxy)-2-methylhex-4-enoyl]-1,3-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-4-benzyl-3-[(2R,4E)-6-(benzyloxy)-2-methylhex-4-enoyl]-1,3-oxazolidin-2-one

There total 1 articles about (4S)-4-benzyl-3-[(2R,4E)-6-(benzyloxy)-2-methylhex-4-enoyl]-1,3-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: 69.0%

(S)-4-benzyl-3-propionyl-2-oxazolidinone (131685-53-5,101711-78-8) + benzyl (2E)-4-bromobut-2-en-1-yl ether (89358-30-5) → (4S)-4-benzyl-3-[(2R,4E)-6-(benzyloxy)-2-methylhex-4-enoyl]-1,3-oxazolidin-2-one (1000050-92-9)

Guidance literature:

(S)-4-benzyl-3-propionyl-2-oxazolidinone; With sodium hexamethyldisilazane; In tetrahydrofuran; hexane; at -78 ℃; for 1.25h;

benzyl (2E)-4-bromobut-2-en-1-yl ether; In tetrahydrofuran; hexane; at -78 - -40 ℃; for 4.5h;

Reference yield:

(4S)-4-benzyl-3-[(2R,4E)-6-(benzyloxy)-2-methylhex-4-enoyl]-1,3-oxazolidin-2-one (1000050-92-9) → (2R,4E)-6-(benzyloxy)-2-methylhex-4-enoic acid (127949-92-2)

Guidance literature:

(4S)-4-benzyl-3-[(2R,4E)-6-(benzyloxy)-2-methylhex-4-enoyl]-1,3-oxazolidin-2-one; With lithium hydroxide; water; dihydrogen peroxide; In tetrahydrofuran; at 0 ℃; for 16.5h;

With sodium dihydrogenphosphate; water;

Reference yield:

(4S)-4-benzyl-3-[(2R,4E)-6-(benzyloxy)-2-methylhex-4-enoyl]-1,3-oxazolidin-2-one (1000050-92-9) → {(1S,2S,4R)-4-(2,2-dimethylpropylcarbamoyl)-1-[4-(2-chlorophenyl)-2,2-dimethyl-5-oxopiperazin-1-ylmethyl]-2-hydroxypentyl}carbamic acid t-butyl ester (1000051-13-7)

Guidance literature:

Multi-step reaction with 11 steps

1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 16.5 h / 0 - 20 °C

2: tetra(n-butyl)ammonium hydrogensulfate; Shi's ketone; Oxone; potassium carbonate; edetate disodium / acetonitrile / 9 h / 0 °C

3: triethylamine / dichloromethane / 3 h / 0 °C

4: sodium azide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 72 h / 60 °C

5: hydrogenchloride; palladium 10% on activated carbon; hydrogen / ethanol; 1,4-dioxane / 6 h / 20 °C

6: triethylamine / tetrahydrofuran; water / 2 h / 0 °C

7: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 0.17 h / 0 °C

8: toluene / 1.5 h / 110 °C

9: caesium carbonate; thiophenol / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

10: triethylamine / dichloromethane / 15 h / 20 °C

11: 2-hydroxypyridin / 3 h / 80 °C

With 2-hydroxypyridin; hydrogenchloride; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; Oxone; sodium azide; Shi's ketone; lithium hydroxide monohydrate; palladium 10% on activated carbon; hydrogen; dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; edetate disodium; potassium carbonate; caesium carbonate; thiophenol; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 2: |Shi Asymmetric Epoxidation / 7: |Mitsunobu Displacement;

DOI:10.1016/j.bmc.2013.03.022

upstream raw materials:

(S)-4-benzyl-3-propionyl-2-oxazolidinone

benzyl (2E)-4-bromobut-2-en-1-yl ether

Downstream raw materials:

(2R,4E)-6-(benzyloxy)-2-methylhex-4-enoic acid

(3R,5S)-5-[(1S)-1-azido-2-(benzyloxy)ethyl]-3-methyldihydrofuran-2(3H)-one

(3R,5S)-5-[(1R)-2-(benzyloxy)-1-hydroxyethyl]-3-methyldihydrofuran-2(3H)-one

(1R)-2-(benzyloxy)-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl methanesulfonate