(3S,4S,8aS,4aR)-4-(2-(tert-butyldiphenylsilyloxy)ethyl)-3,4a,8,8-tetramethylperhydro-2-naphthalenone

Base Information

Chemical Name:(3S,4S,8aS,4aR)-4-(2-(tert-butyldiphenylsilyloxy)ethyl)-3,4a,8,8-tetramethylperhydro-2-naphthalenone
CAS No.:378197-95-6
Molecular Formula:C₃₂H₄₆O₂Si
Molecular Weight:490.802
Hs Code.:

Synonyms:(3S,4S,8aS,4aR)-4-(2-(tert-butyldiphenylsilyloxy)ethyl)-3,4a,8,8-tetramethylperhydro-2-naphthalenone

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Chemical Property of (3S,4S,8aS,4aR)-4-(2-(tert-butyldiphenylsilyloxy)ethyl)-3,4a,8,8-tetramethylperhydro-2-naphthalenone

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Technology Process of (3S,4S,8aS,4aR)-4-(2-(tert-butyldiphenylsilyloxy)ethyl)-3,4a,8,8-tetramethylperhydro-2-naphthalenone

There total 5 articles about (3S,4S,8aS,4aR)-4-(2-(tert-butyldiphenylsilyloxy)ethyl)-3,4a,8,8-tetramethylperhydro-2-naphthalenone 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: 88.0%

: 378197-94-5
(2R,4S,4aR,8aS)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3,4a,8,8-tetramethyl-decahydro-naphthalen-2-ol

: 378197-95-6
(3S,4S,8aS,4aR)-4-(2-(tert-butyldiphenylsilyloxy)ethyl)-3,4a,8,8-tetramethylperhydro-2-naphthalenone

Guidance literature:: (2R,4S,4aR,8aS)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3,4a,8,8-tetramethyl-decahydro-naphthalen-2-ol; With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 12h;

With sodium methylate; In methanol; at 20 ℃; Further stages.;
DOI:10.1021/jo010154c

Reference yield:

: 38419-75-9
(1R,2R,4aS,8aS)-1-(2-hydroxyethyl)-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol

: 378197-95-6
(3S,4S,8aS,4aR)-4-(2-(tert-butyldiphenylsilyloxy)ethyl)-3,4a,8,8-tetramethylperhydro-2-naphthalenone

Guidance literature:: Multi-step reaction with 4 steps

1.1: 99 percent / imidazole / dimethylformamide / 1 h / 20 °C

2.1: SOCl₂; 4-DMAP / pyridine / -50 - 0 °C

2.2: 62 percent / SeO₂; salicylic acid; tBuOOH / CH₂Cl₂ / 48 h / 20 °C

3.1: 80 percent / H₂ / Pd/C / ethanol / 12 h / 20 °C / 760.05 Torr

4.1: PCC / CH₂Cl₂ / 12 h / 20 °C

4.2: 88 percent / sodium methylate / methanol / 20 °C

With 1H-imidazole; dmap; thionyl chloride; hydrogen; pyridinium chlorochromate; palladium on activated charcoal; In pyridine; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo010154c

Reference yield:

: 564-20-5,1216-84-8,30450-17-0,58976-28-6,64090-92-2,67844-42-2,79768-41-5,79768-42-6,86688-27-9,86688-28-0,95406-08-9,98719-44-9,98719-46-1,131831-65-7,140851-80-5
(3aR)-(+)-sclareolide

: 378197-95-6
(3S,4S,8aS,4aR)-4-(2-(tert-butyldiphenylsilyloxy)ethyl)-3,4a,8,8-tetramethylperhydro-2-naphthalenone

Guidance literature:: Multi-step reaction with 5 steps

1.1: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / 0 °C

2.1: 99 percent / imidazole / dimethylformamide / 1 h / 20 °C

3.1: SOCl₂; 4-DMAP / pyridine / -50 - 0 °C

3.2: 62 percent / SeO₂; salicylic acid; tBuOOH / CH₂Cl₂ / 48 h / 20 °C

4.1: 80 percent / H₂ / Pd/C / ethanol / 12 h / 20 °C / 760.05 Torr

5.1: PCC / CH₂Cl₂ / 12 h / 20 °C

5.2: 88 percent / sodium methylate / methanol / 20 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; thionyl chloride; hydrogen; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo010154c