(1S,4S)-N-but-3-enyl-N-[4-(tert-butyldimethylsilanyloxy)cyclopent-2-enyl]-4-methylbenzene sulfonamide

Base Information

• Chemical Name: (1S,4S)-N-but-3-enyl-N-[4-(tert-butyldimethylsilanyloxy)cyclopent-2-enyl]-4-methylbenzene sulfonamide
• CAS No.: 245092-61-9
• Molecular Formula: C₂₂H₃₅NO₃SSi
• Molecular Weight: 421.676

Synonyms:(1S,4S)-N-but-3-enyl-N-[4-(tert-butyldimethylsilanyloxy)cyclopent-2-enyl]-4-methylbenzene sulfonamide

Chemical Property of (1S,4S)-N-but-3-enyl-N-[4-(tert-butyldimethylsilanyloxy)cyclopent-2-enyl]-4-methylbenzene sulfonamide

Chemical Property:

Purity/Quality:

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Technology Process of (1S,4S)-N-but-3-enyl-N-[4-(tert-butyldimethylsilanyloxy)cyclopent-2-enyl]-4-methylbenzene sulfonamide

There total 4 articles about (1S,4S)-N-but-3-enyl-N-[4-(tert-butyldimethylsilanyloxy)cyclopent-2-enyl]-4-methylbenzene sulfonamide 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: 87.0%

N-tosyl-3-butenylamine (10285-80-0) + (1R,4S)-4-(tert-butyldimethylsilyloxy)cyclopent-2-enol (120520-91-4) → (1S,4S)-N-but-3-enyl-N-[4-(tert-butyldimethylsilanyloxy)cyclopent-2-enyl]-4-methylbenzene sulfonamide (245092-61-9)

Guidance literature:

With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine; In benzene;

DOI:10.1016/S0040-4020(99)00299-9

Reference yield:

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate (60410-16-4) → (1S,4S)-N-but-3-enyl-N-[4-(tert-butyldimethylsilanyloxy)cyclopent-2-enyl]-4-methylbenzene sulfonamide (245092-61-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / imidazole / dimethylformamide / 25 °C

2: 100 percent / NEt₃; CH₃OH / 18 h / 25 °C

3: 87 percent / tributylphosphine; azodicarboxylic dipiperidide / benzene

With 1H-imidazole; methanol; tributylphosphine; triethylamine; 1,1'-azodicarbonyl-dipiperidine; In N,N-dimethyl-formamide; benzene; 1: Substitution / 2: Hydrolysis / 3: Mitsunobu reaction;

DOI:10.1016/S0040-4020(99)00299-9

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (1S,4S)-N-but-3-enyl-N-[4-(tert-butyldimethylsilanyloxy)cyclopent-2-enyl]-4-methylbenzene sulfonamide (245092-61-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / imidazole / dimethylformamide / 25 °C

2: 100 percent / NEt₃; CH₃OH / 18 h / 25 °C

3: 87 percent / tributylphosphine; azodicarboxylic dipiperidide / benzene

With 1H-imidazole; methanol; tributylphosphine; triethylamine; 1,1'-azodicarbonyl-dipiperidine; In N,N-dimethyl-formamide; benzene; 1: Substitution / 2: Hydrolysis / 3: Mitsunobu reaction;

DOI:10.1016/S0040-4020(99)00299-9

upstream raw materials:

N-tosyl-3-butenylamine

(1R,4S)-4-(tert-butyldimethylsilyloxy)cyclopent-2-enol

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate

(1R,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-cyclopentene-1-yl acetate

Downstream raw materials:

6-[2-(tert-butyldimethylsilanyloxy)but-3-enyl]-1-(toluene-4-sulfonyl)-1,2,5,6-tetrahydropyridine

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