(-)-(4aS,7R,8aR)-7-(tert-butyldimethylsilyl)oxy-5-methylene-8a-methyl-decahydronaphthalen-2-one

Base Information

Chemical Name:(-)-(4aS,7R,8aR)-7-(tert-butyldimethylsilyl)oxy-5-methylene-8a-methyl-decahydronaphthalen-2-one
CAS No.:89949-94-0
Molecular Formula:C₁₈H₃₂O₂Si
Molecular Weight:308.536
Hs Code.:

Synonyms:(-)-(4aS,7R,8aR)-7-(tert-butyldimethylsilyl)oxy-5-methylene-8a-methyl-decahydronaphthalen-2-one

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Chemical Property of (-)-(4aS,7R,8aR)-7-(tert-butyldimethylsilyl)oxy-5-methylene-8a-methyl-decahydronaphthalen-2-one

Chemical Property:

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Technology Process of (-)-(4aS,7R,8aR)-7-(tert-butyldimethylsilyl)oxy-5-methylene-8a-methyl-decahydronaphthalen-2-one

There total 1 articles about (-)-(4aS,7R,8aR)-7-(tert-butyldimethylsilyl)oxy-5-methylene-8a-methyl-decahydronaphthalen-2-one 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:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 89949-92-8
(-)-(4aS,7R,8aR)-7-methylsulfonyloxy-5-methylene-8a-methyl-decahydronaphthalen-2-one

: 67-71-0
dimethylsulfone

: 89949-94-0
(-)-(4aS,7R,8aR)-7-(tert-butyldimethylsilyl)oxy-5-methylene-8a-methyl-decahydronaphthalen-2-one

: 89949-93-9
(4aS,7S,8aR)-7-Hydroxy-8a-methyl-5-methylene-octahydro-naphthalen-2-one

Guidance literature:: With 1H-imidazole; dmap; 18-crown-6 ether; Yield given. Multistep reaction. Yields of byproduct given; 1) DMSO, DME, 0 deg C, 1 h; 2) DMF, r.t., 48 h;
DOI:10.1016/0040-4020(89)80093-6

Reference yield:

: 89949-94-0
(-)-(4aS,7R,8aR)-7-(tert-butyldimethylsilyl)oxy-5-methylene-8a-methyl-decahydronaphthalen-2-one

: 5938-03-4
ivalin

Guidance literature:: Multi-step reaction with 6 steps

1: 1) LDA; 2) HMPA / 1) THF, -78 deg C, 20 min; 2) THF, 1 h

2: 76 percent / potassium tert-butoxide / tetrahydrofuran / 0.17 h / Ambient temperature

3: 81 percent / sodium borohydride / methanol / 1 h / -78 °C

4: 74 percent / LDA / tetrahydrofuran / 15 h / -78 °C

5: 50 percent / pyridine, diisopropylethylamine, methanesolfonyl chloride / CH₂Cl₂ / 0.25 h / 0 °C

6: 78 percent / 40percent HF / acetonitrile / 0.17 h / Ambient temperature

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; hydrogen fluoride; potassium tert-butylate; methanesulfonyl chloride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1016/0040-4020(89)80093-6