(-)-(1S,3S,5S)-5-[N-allyl-N-(2-nitrobenzenesulfonyl)amino]-3-hydroxycyclohept-6-enyl acetate

Base Information

• Chemical Name: (-)-(1S,3S,5S)-5-[N-allyl-N-(2-nitrobenzenesulfonyl)amino]-3-hydroxycyclohept-6-enyl acetate
• CAS No.: 501416-05-3
• Molecular Formula: C₁₈H₂₂N₂O₇S
• Molecular Weight: 410.448

Synonyms:(-)-(1S,3S,5S)-5-[N-allyl-N-(2-nitrobenzenesulfonyl)amino]-3-hydroxycyclohept-6-enyl acetate

Chemical Property of (-)-(1S,3S,5S)-5-[N-allyl-N-(2-nitrobenzenesulfonyl)amino]-3-hydroxycyclohept-6-enyl acetate

Chemical Property:

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Technology Process of (-)-(1S,3S,5S)-5-[N-allyl-N-(2-nitrobenzenesulfonyl)amino]-3-hydroxycyclohept-6-enyl acetate

There total 3 articles about (-)-(1S,3S,5S)-5-[N-allyl-N-(2-nitrobenzenesulfonyl)amino]-3-hydroxycyclohept-6-enyl 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: 85.0%

(-)-(1S,3S,5S)-5-(N-allyl-N-(2-nitrobenzenesulfonyl)amino)-3-(tert-butyl-dimethylsilanyloxy)cyclohept-6-enyl acetate (501415-98-1) → (-)-(1S,3S,5S)-5-[N-allyl-N-(2-nitrobenzenesulfonyl)amino]-3-hydroxycyclohept-6-enyl acetate (501416-05-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1016/S0040-4020(02)00832-3

Reference yield:

(1R,4S,6S)-4-acetoxy-6-[(tert-butyldimethylsilyl)oxy]-2-cyclohepten-1-ol (134734-52-4) → (-)-(1S,3S,5S)-5-[N-allyl-N-(2-nitrobenzenesulfonyl)amino]-3-hydroxycyclohept-6-enyl acetate (501416-05-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / PPh₃; DEAD / tetrahydrofuran / 18 h / 0 - 20 °C

2: 85 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

With tetrabutyl ammonium fluoride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1: Mitsunobu reaction;

DOI:10.1016/S0040-4020(02)00832-3

Reference yield:

N-allyl-o-nitrobenzenesulfonamide (65118-17-4) → (-)-(1S,3S,5S)-5-[N-allyl-N-(2-nitrobenzenesulfonyl)amino]-3-hydroxycyclohept-6-enyl acetate (501416-05-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / PPh₃; DEAD / tetrahydrofuran / 18 h / 0 - 20 °C

2: 85 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

With tetrabutyl ammonium fluoride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1: Mitsunobu reaction;

DOI:10.1016/S0040-4020(02)00832-3

upstream raw materials:

(-)-(1S,3S,5S)-5-(N-allyl-N-(2-nitrobenzenesulfonyl)amino)-3-(tert-butyl-dimethylsilanyloxy)cyclohept-6-enyl acetate

(1R,4S,6S)-4-acetoxy-6-[(tert-butyldimethylsilyl)oxy]-2-cyclohepten-1-ol

N-allyl-o-nitrobenzenesulfonamide

Downstream raw materials:

(-)-(1S,3S,5S)-3-allyloxy-5-[N-allyl-N-(2-nitrobenzenesulfonyl)amino]cyclohept-6-enyl acetate

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