(4aR,5R,8aS)-5-[1-(tert-butyl)-1,1-(diphenylsilyl)oxy]-8a-methylperhydro-1-naphthalenone

Base Information

Chemical Name:(4aR,5R,8aS)-5-[1-(tert-butyl)-1,1-(diphenylsilyl)oxy]-8a-methylperhydro-1-naphthalenone
CAS No.:312584-22-8
Molecular Formula:C₂₇H₃₆O₂Si
Molecular Weight:420.667
Hs Code.:

Synonyms:(4aR,5R,8aS)-5-[1-(tert-butyl)-1,1-(diphenylsilyl)oxy]-8a-methylperhydro-1-naphthalenone

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Chemical Property of (4aR,5R,8aS)-5-[1-(tert-butyl)-1,1-(diphenylsilyl)oxy]-8a-methylperhydro-1-naphthalenone

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Technology Process of (4aR,5R,8aS)-5-[1-(tert-butyl)-1,1-(diphenylsilyl)oxy]-8a-methylperhydro-1-naphthalenone

There total 9 articles about (4aR,5R,8aS)-5-[1-(tert-butyl)-1,1-(diphenylsilyl)oxy]-8a-methylperhydro-1-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: 98.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 312584-14-8
(4aR,5R,8aS)-5-hydroxy-8a-methylperhydro-1-naphthalenone

: 312584-22-8
(4aR,5R,8aS)-5-[1-(tert-butyl)-1,1-(diphenylsilyl)oxy]-8a-methylperhydro-1-naphthalenone

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 48h;
DOI:10.1002/1099-0690(200010)2000:20<3427::aid-ejoc3427>3.3.co;2-o

Reference yield:

: 33878-99-8
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione

: 312584-22-8
(4aR,5R,8aS)-5-[1-(tert-butyl)-1,1-(diphenylsilyl)oxy]-8a-methylperhydro-1-naphthalenone

Guidance literature:: Multi-step reaction with 9 steps

1.1: 4.53 g / p-TsOH / acetic acid / 5 h / 20 °C

2.1: 5.33 g / p-TsOH / toluene / 12 h / Heating; Dean-Stark apparatus

3.1: Na; liq. NH₃ / 1 h

4.1: BH₃*THF / 15 h / 0 - 20 °C

4.2: 83 percent / NaOH (3N); H₂O₂ (30 percent) / tetrahydrofuran / 4 h

5.1: 96 percent / mol. sieves; NMO; TPAP / CH₂Cl₂ / 3 h / 20 °C

6.1: 85 percent / NaOMe / methanol / 24 h / 20 °C

7.1: Li; liq. NH₃ / methanol / 2 h / -78 °C

8.1: p-TsOH; H₂O; Me₂CO / 10 h / 20 °C

9.1: 98 percent / imidazole / dimethylformamide / 48 h / 20 °C

With 1H-imidazole; N-methyl-2-indolinone; molecular sieve; tetrapropylammonium perruthennate; borane-THF; ammonia; water; sodium methylate; sodium; lithium; toluene-4-sulfonic acid; acetone; In methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; toluene; 1.1: Cyclization / 2.1: Etherification / 3.1: Reduction / 4.1: Addition / 4.2: Oxidation / 5.1: Oxidation / 6.1: Isomerization / 7.1: Reduction / 8.1: Hydrolysis / 9.1: Substitution;
DOI:10.1002/1099-0690(200010)2000:20<3427::aid-ejoc3427>3.3.co;2-o

Reference yield:

: 145632-33-3
(S)-7a′-methyl-2′,3′,7′,7a′-tetrahydrospiro[[1,3]dithiolane-2,5′-inden]-1′(6′H)-one

: 312584-22-8
(4aR,5R,8aS)-5-[1-(tert-butyl)-1,1-(diphenylsilyl)oxy]-8a-methylperhydro-1-naphthalenone

Guidance literature:: Multi-step reaction with 8 steps

1.1: 5.33 g / p-TsOH / toluene / 12 h / Heating; Dean-Stark apparatus

2.1: Na; liq. NH₃ / 1 h

3.1: BH₃*THF / 15 h / 0 - 20 °C

3.2: 83 percent / NaOH (3N); H₂O₂ (30 percent) / tetrahydrofuran / 4 h

4.1: 96 percent / mol. sieves; NMO; TPAP / CH₂Cl₂ / 3 h / 20 °C

5.1: 85 percent / NaOMe / methanol / 24 h / 20 °C

6.1: Li; liq. NH₃ / methanol / 2 h / -78 °C

7.1: p-TsOH; H₂O; Me₂CO / 10 h / 20 °C

8.1: 98 percent / imidazole / dimethylformamide / 48 h / 20 °C

With 1H-imidazole; N-methyl-2-indolinone; molecular sieve; tetrapropylammonium perruthennate; borane-THF; ammonia; water; sodium methylate; sodium; lithium; toluene-4-sulfonic acid; acetone; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Etherification / 2.1: Reduction / 3.1: Addition / 3.2: Oxidation / 4.1: Oxidation / 5.1: Isomerization / 6.1: Reduction / 7.1: Hydrolysis / 8.1: Substitution;
DOI:10.1002/1099-0690(200010)2000:20<3427::aid-ejoc3427>3.3.co;2-o