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

Base Information

• Chemical Name: (3R_*,4S_*)-4-<(tert-butyldimethylsilyl)oxy>-6,10-dimethyl-2-methylene-3-(mesyloxy)-N-phenyl-9-undecenamide
• CAS No.: 118336-67-7
• Molecular Formula: C₂₇H₄₅NO₅SSi
• Molecular Weight: 523.81

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

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

Chemical Property:

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

There total 10 articles about (3R_*,4S_*)-4-<(tert-butyldimethylsilyl)oxy>-6,10-dimethyl-2-methylene-3-(mesyloxy)-N-phenyl-9-undecenamide 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: 35.0%

4-<(tert-butyldimethylsilyl)oxy>-3-hydroxy-6,10-dimethyl-2-methylene-N-phenyl-9-undecenamide (118336-64-4) + methanesulfonyl chloride (124-63-0) → (3R*,4R*)-4-<(tert-butyldimethylsilyl)oxy>-6,10-dimethyl-2-methylene-3-(mesyloxy)-N-phenyl-9-undecenamide (118336-67-7) + (3R*,4S*)-4-<(tert-butyldimethylsilyl)oxy>-6,10-dimethyl-2-methylene-3-(mesyloxy)-N-phenyl-9-undecenamide (118336-67-7)

Guidance literature:

With triethylamine; In dichloromethane; for 0.5h;

DOI:10.1021/jo00262a020

Reference yield: 35.0%

4-<(tert-butyldimethylsilyl)oxy>-3-hydroxy-6,10-dimethyl-2-methylene-N-phenyl-9-undecenamide (118336-64-4) + methanesulfonyl chloride (124-63-0) → (3R*,4R*)-4-<(tert-butyldimethylsilyl)oxy>-6,10-dimethyl-2-methylene-3-(mesyloxy)-N-phenyl-9-undecenamide (118336-67-7) + (3R*,4S*)-4-<(tert-butyldimethylsilyl)oxy>-6,10-dimethyl-2-methylene-3-(mesyloxy)-N-phenyl-9-undecenamide (118336-67-7)

Guidance literature:

With triethylamine; In dichloromethane; for 0.5h;

DOI:10.1021/jo00262a020

Reference yield:

4-hydroxy-6,10-dimethyl-2-methylene-N-phenyl-3-(phenylsulfonyl)-9-undecenamide (118336-40-6) → (3R*,4R*)-4-<(tert-butyldimethylsilyl)oxy>-6,10-dimethyl-2-methylene-3-(mesyloxy)-N-phenyl-9-undecenamide (118336-67-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent

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

3: 84 percent / MCPBA / CH₂Cl₂ / 1 h / -78 °C

4: 33 percent / Et₃N / CH₂Cl₂ / 0.5 h

With sodium tetrahydroborate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/jo00262a020

upstream raw materials:

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

methanesulfonyl chloride

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

4-<(tert-butyldimethylsilyl)oxy>-6,10-dimethyl-N-phenyl-2-<(phenylseleno)methyl>-2,9-undecadienamide

Downstream raw materials:

(3R_*,4S_*)-3,4-epoxy-6,10-dimethyl-2-methylene-N-phenyl-9-undecenamide

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

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

(3R_*,4R_*)-3,4-epoxy-6,10-dimethyl-2-methylene-N-phenyl-9-undecenamide

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