(4aS,8aS,2R,4R)-4-(2-[tert-butyldiphenylsilyloxy]ethyl)-4a,8,8,trimethyl-3-methyleneperhydro-2-naphthalenol

Base Information

Chemical Name:(4aS,8aS,2R,4R)-4-(2-[tert-butyldiphenylsilyloxy]ethyl)-4a,8,8,trimethyl-3-methyleneperhydro-2-naphthalenol
CAS No.:378197-93-4
Molecular Formula:C₃₂H₄₆O₂Si
Molecular Weight:490.802
Hs Code.:

Synonyms:(4aS,8aS,2R,4R)-4-(2-[tert-butyldiphenylsilyloxy]ethyl)-4a,8,8,trimethyl-3-methyleneperhydro-2-naphthalenol

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Chemical Property of (4aS,8aS,2R,4R)-4-(2-[tert-butyldiphenylsilyloxy]ethyl)-4a,8,8,trimethyl-3-methyleneperhydro-2-naphthalenol

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Technology Process of (4aS,8aS,2R,4R)-4-(2-[tert-butyldiphenylsilyloxy]ethyl)-4a,8,8,trimethyl-3-methyleneperhydro-2-naphthalenol

There total 3 articles about (4aS,8aS,2R,4R)-4-(2-[tert-butyldiphenylsilyloxy]ethyl)-4a,8,8,trimethyl-3-methyleneperhydro-2-naphthalenol 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: 62.0%

: 378197-91-2
(4aS,8aS,1R,2R)-1-(2-(tert-butyldiphenylsilyloxy)ethyl)-2,5,5,8a-tetramethylperhydro-2-naphthalenol

: 378197-93-4
(4aS,8aS,2R,4R)-4-(2-[tert-butyldiphenylsilyloxy]ethyl)-4a,8,8,trimethyl-3-methyleneperhydro-2-naphthalenol

Guidance literature:: (4aS,8aS,1R,2R)-1-(2-(tert-butyldiphenylsilyloxy)ethyl)-2,5,5,8a-tetramethylperhydro-2-naphthalenol; With dmap; thionyl chloride; In pyridine; at -50 - 0 ℃;

With tert.-butylhydroperoxide; selenium(IV) oxide; salicylic acid; In dichloromethane; at 20 ℃; for 48h; 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

: 378197-93-4
(4aS,8aS,2R,4R)-4-(2-[tert-butyldiphenylsilyloxy]ethyl)-4a,8,8,trimethyl-3-methyleneperhydro-2-naphthalenol

Guidance literature:: Multi-step reaction with 2 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

With 1H-imidazole; dmap; thionyl chloride; In pyridine; 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

: 378197-93-4
(4aS,8aS,2R,4R)-4-(2-[tert-butyldiphenylsilyloxy]ethyl)-4a,8,8,trimethyl-3-methyleneperhydro-2-naphthalenol

Guidance literature:: Multi-step reaction with 3 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

With 1H-imidazole; dmap; lithium aluminium tetrahydride; thionyl chloride; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide;
DOI:10.1021/jo010154c