N,N-dicyclohexyl-C-[7,7-dimethyl-2-(1-triisopropylsilanyloxy-vinylsulfanyl)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide

Base Information

• Chemical Name: N,N-dicyclohexyl-C-[7,7-dimethyl-2-(1-triisopropylsilanyloxy-vinylsulfanyl)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide
• CAS No.: 324016-39-9
• Molecular Formula: C₃₃H₆₁NO₃S₂Si
• Molecular Weight: 612.07

Synonyms:N,N-dicyclohexyl-C-[7,7-dimethyl-2-(1-triisopropylsilanyloxy-vinylsulfanyl)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide

Chemical Property of N,N-dicyclohexyl-C-[7,7-dimethyl-2-(1-triisopropylsilanyloxy-vinylsulfanyl)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide

Chemical Property:

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Technology Process of N,N-dicyclohexyl-C-[7,7-dimethyl-2-(1-triisopropylsilanyloxy-vinylsulfanyl)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide

There total 3 articles about N,N-dicyclohexyl-C-[7,7-dimethyl-2-(1-triisopropylsilanyloxy-vinylsulfanyl)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide 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:

N,N-dicyclohexylcamphor-10-sulfonamide (96303-87-6) → N,N-dicyclohexyl-C-[7,7-dimethyl-2-(1-triisopropylsilanyloxy-vinylsulfanyl)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide (324016-39-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 4-methoxy-phenylthionophosphine sulfide / toluene / 0.5 h / Heating

1.2: 55.6 percent / pyridine / 48 h / Heating

2.1: 83 percent / NaBH₄ / tetrahydrofuran; propan-2-ol / 0 - 20 °C

3.1: 77.3 percent / pyridine; DMAP / CH₂Cl₂ / 0 - 20 °C

4.1: NaHMDS / tetrahydrofuran / 4 h / -78 °C

With pyridine; dmap; sodium tetrahydroborate; 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide; sodium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; isopropyl alcohol; toluene; 1.1: Substitution / 1.2: Substitution / 2.1: Reduction / 3.1: Acetylation / 4.1: enolization; silylation;

DOI:10.1016/S0040-4020(00)00894-2

Reference yield:

N,N-dicyclohexyl-C-(7,7-dimethyl-2-thioxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonamide (324016-34-4) → N,N-dicyclohexyl-C-[7,7-dimethyl-2-(1-triisopropylsilanyloxy-vinylsulfanyl)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide (324016-39-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / NaBH₄ / tetrahydrofuran; propan-2-ol / 0 - 20 °C

2: 77.3 percent / pyridine; DMAP / CH₂Cl₂ / 0 - 20 °C

3: NaHMDS / tetrahydrofuran / 4 h / -78 °C

With pyridine; dmap; sodium tetrahydroborate; sodium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; isopropyl alcohol; 1: Reduction / 2: Acetylation / 3: enolization; silylation;

DOI:10.1016/S0040-4020(00)00894-2

Reference yield:

N,N-dicyclohexyl-C-(2-mercapto-7,7-dimethyl-bicyclo[2.2.1]hept-1-yl)-methanesulfonamide (324016-35-5) → N,N-dicyclohexyl-C-[7,7-dimethyl-2-(1-triisopropylsilanyloxy-vinylsulfanyl)-bicyclo[2.2.1]hept-1-yl]-methanesulfonamide (324016-39-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 77.3 percent / pyridine; DMAP / CH₂Cl₂ / 0 - 20 °C

2: NaHMDS / tetrahydrofuran / 4 h / -78 °C

With pyridine; dmap; sodium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 1: Acetylation / 2: enolization; silylation;

DOI:10.1016/S0040-4020(00)00894-2

upstream raw materials:

N,N-dicyclohexylcamphor-10-sulfonamide

N,N-dicyclohexyl-C-(7,7-dimethyl-2-thioxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonamide

N,N-dicyclohexyl-C-(2-mercapto-7,7-dimethyl-bicyclo[2.2.1]hept-1-yl)-methanesulfonamide

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