(4R_*)-4-<(1S_*)-1-hydroxy-3,7-dimethyl-6-octenyl>-2-methylene-N-phenyl-2-azetidinone

Base Information

• Chemical Name: (4R_*)-4-<(1S_*)-1-hydroxy-3,7-dimethyl-6-octenyl>-2-methylene-N-phenyl-2-azetidinone
• CAS No.: 118336-76-8
• Molecular Formula: C₂₀H₂₇NO₂
• Molecular Weight: 313.44

Synonyms:(4R_*)-4-<(1S_*)-1-hydroxy-3,7-dimethyl-6-octenyl>-2-methylene-N-phenyl-2-azetidinone

Chemical Property of (4R_*)-4-<(1S_*)-1-hydroxy-3,7-dimethyl-6-octenyl>-2-methylene-N-phenyl-2-azetidinone

Chemical Property:

Purity/Quality:

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Technology Process of (4R_*)-4-<(1S_*)-1-hydroxy-3,7-dimethyl-6-octenyl>-2-methylene-N-phenyl-2-azetidinone

There total 13 articles about (4R_*)-4-<(1S_*)-1-hydroxy-3,7-dimethyl-6-octenyl>-2-methylene-N-phenyl-2-azetidinone 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: 23.0%

(3R*,4R*)-4-<(tert-butyldimethylsilyl)oxy>-6,10-dimethyl-2-methylene-3-(mesyloxy)-N-phenyl-9-undecenamide (118336-67-7) → (3R*,4S*)-3,4-epoxy-6,10-dimethyl-2-methylene-N-phenyl-9-undecenamide (118336-75-7) + (4R*)-4-<(1S*)-1-hydroxy-3,7-dimethyl-6-octenyl>-2-methylene-N-phenyl-2-azetidinone (118336-76-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 4h;

DOI:10.1021/jo00262a020

Reference yield: 10.0%

(3R*,4S*)-4-<(tert-butyldimethylsilyl)oxy>-6,10-dimethyl-2-methylene-3-(mesyloxy)-N-phenyl-9-undecenamide (118336-67-7) → (3R*,4R*)-3,4-epoxy-6,10-dimethyl-2-methylene-N-phenyl-9-undecenamide (118336-75-7) + (4R*)-4-<(1R*)-1-hydroxy-3,7-dimethyl-6-octenyl>-2-methylene-N-phenyl-2-azetidinone (118336-76-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 4h;

DOI:10.1021/jo00262a020

Reference yield:

3,7-dimethyl-oct-6-enal (106-23-0,26489-02-1) → (4R*)-4-<(1S*)-1-hydroxy-3,7-dimethyl-6-octenyl>-2-methylene-N-phenyl-2-azetidinone (118336-76-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) n-BuLi / 1.) THF, HMPA, -78 deg C, 1 h, 2.) -78 deg C, 2 h

2: 95 percent

3: 91 percent / NaBH₄ / ethanol; tetrahydrofuran / 2 h / Ambient temperature

4: 84 percent / MCPBA / CH₂Cl₂ / 1 h / -78 °C

5: 33 percent / Et₃N / CH₂Cl₂ / 0.5 h

6: 23 percent / n-Bu₄NF / tetrahydrofuran / 4 h / 0 °C

With sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/jo00262a020

upstream raw materials:

(3R_*,4R_*)-4-<(tert-butyldimethylsilyl)oxy>-6,10-dimethyl-2-methylene-3-(mesyloxy)-N-phenyl-9-undecenamide

3,7-dimethyl-oct-6-enal

4-<(tert-butyldimethylsilyl)oxy>-3-hydroxy-6,10-dimethyl-2-methylene-N-phenyl-9-undecenamide

4-hydroxy-6,10-dimethyl-2-methylene-N-phenyl-3-(phenylsulfonyl)-9-undecenamide

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