(2S,3S,4E)-2-[(1E)-3-(benzyloxy)-1-methylprop-1-en-1-yl]-3-methyl-12-oxaazacyclododec-4-en-6-yl acetate

Base Information

• Chemical Name: (2S,3S,4E)-2-[(1E)-3-(benzyloxy)-1-methylprop-1-en-1-yl]-3-methyl-12-oxaazacyclododec-4-en-6-yl acetate
• CAS No.: 1072091-22-5
• Molecular Formula: C₂₅H₃₅NO₄
• Molecular Weight: 413.557
• Mol file: 1072091-22-5.mol

Synonyms:(2S,3S,4E)-2-[(1E)-3-(benzyloxy)-1-methylprop-1-en-1-yl]-3-methyl-12-oxaazacyclododec-4-en-6-yl acetate

Chemical Property of (2S,3S,4E)-2-[(1E)-3-(benzyloxy)-1-methylprop-1-en-1-yl]-3-methyl-12-oxaazacyclododec-4-en-6-yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4E)-2-[(1E)-3-(benzyloxy)-1-methylprop-1-en-1-yl]-3-methyl-12-oxaazacyclododec-4-en-6-yl acetate

There total 12 articles about (2S,3S,4E)-2-[(1E)-3-(benzyloxy)-1-methylprop-1-en-1-yl]-3-methyl-12-oxaazacyclododec-4-en-6-yl acetate 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:

C23H33NO3 (1072091-26-9) + acetic anhydride (108-24-7) → (2S,3S,4E)-2-[(1E)-3-(benzyloxy)-1-methylprop-1-en-1-yl]-3-methyl-12-oxaazacyclododec-4-en-6-yl acetate (1072091-22-5)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1h;

Reference yield:

ethyl (2E,4S,5R)-6-{[tert-butyl(dimethyl)silyl]oxy}-4-[(4-methoxyphenyl)amino]-3,5-dimethylhex-2-enoate (1072091-06-5) → (2S,3S,4E)-2-[(1E)-3-(benzyloxy)-1-methylprop-1-en-1-yl]-3-methyl-12-oxaazacyclododec-4-en-6-yl acetate (1072091-22-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.5 h / -78 °C

1.2: 1 h / 0 °C

2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C

2.2: 19 h / 20 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C

4.1: sulfuric acid; periodic acid / water; acetonitrile / 1.5 h / 20 °C

4.2: 8 h / 20 °C

5.1: Dess-Martin periodane / dichloromethane / 0.17 h / 20 °C

6.1: chromium dichloride / tetrahydrofuran / 5.5 h / 0 - 20 °C

7.1: dichloromethane / 3 h / 20 °C

8.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 1.5 h / 20 °C

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C

10.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C

11.1: chromium dichloride / nickel dichloride / N,N-dimethyl-formamide / 3 h / 20 °C

12.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C

With chromium dichloride; dmap; sulfuric acid; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; benzotriazol-1-ol; Dess-Martin periodane; periodic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; nickel dichloride; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 11.1: Nozaki-Hiyama-Kishi Coupling;

Reference yield:

tert-butyl {(1S,2E)-4-(benzyloxy)-1-[(1R)-2-hydroxy-1-methylethyl]-2-methylbut-2-en-1-yl}carbamate (1072091-14-5) → (2S,3S,4E)-2-[(1E)-3-(benzyloxy)-1-methylprop-1-en-1-yl]-3-methyl-12-oxaazacyclododec-4-en-6-yl acetate (1072091-22-5)

Guidance literature:

Multi-step reaction with 8 steps

1: Dess-Martin periodane / dichloromethane / 0.17 h / 20 °C

2: chromium dichloride / tetrahydrofuran / 5.5 h / 0 - 20 °C

3: dichloromethane / 3 h / 20 °C

4: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 1.5 h / 20 °C

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C

6: Dess-Martin periodane / dichloromethane / 1 h / 20 °C

7: chromium dichloride / nickel dichloride / N,N-dimethyl-formamide / 3 h / 20 °C

8: dmap; triethylamine / dichloromethane / 1 h / 20 °C

With chromium dichloride; dmap; tetrabutyl ammonium fluoride; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; nickel dichloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 7: Nozaki-Hiyama-Kishi Coupling;

upstream raw materials:

C₂₃H₃₃NO₃

acetic anhydride

tert-butyl {(1S,2E)-4-(benzyloxy)-1-[(1R)-2-hydroxy-1-methylethyl]-2-methylbut-2-en-1-yl}carbamate

(2R,3S,4E)-6-(benzyloxy)-3-[(4-methoxyphenyl)amino]-2,4-dimethylhex-4-en-1-ol