(4aR,5R,8R,8aR)-5-{[tert-butyl(dimethyl)silyl]oxy}-8-hydroxy-4a,8-dimethyloctahydronaphthalen-2(1H)-one

Base Information

• Chemical Name: (4aR,5R,8R,8aR)-5-{[tert-butyl(dimethyl)silyl]oxy}-8-hydroxy-4a,8-dimethyloctahydronaphthalen-2(1H)-one
• CAS No.: 136379-65-2
• Molecular Formula: C₁₈H₃₄O₃Si
• Molecular Weight: 326.552
• Mol file: 136379-65-2.mol

Synonyms:2(1H)-Naphthalenone,5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]octahydro-8-hydroxy-4a,8-dimethyl-,(4aa,5a,8a,8ab)- (9CI); 2(1H)-Naphthalenone,5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]octahydro-8-hydroxy-4a,8-dimethyl-,(4aa,5a,8a,8ab)-(?à)-

Chemical Property of (4aR,5R,8R,8aR)-5-{[tert-butyl(dimethyl)silyl]oxy}-8-hydroxy-4a,8-dimethyloctahydronaphthalen-2(1H)-one

Chemical Property:

• Vapor Pressure: 2.37E-07mmHg at 25°C
• Boiling Point: 380.5°Cat760mmHg
• Flash Point: 183.9°C
• Density: 1g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (4aR,5R,8R,8aR)-5-{[tert-butyl(dimethyl)silyl]oxy}-8-hydroxy-4a,8-dimethyloctahydronaphthalen-2(1H)-one

There total 4 articles about (4aR,5R,8R,8aR)-5-{[tert-butyl(dimethyl)silyl]oxy}-8-hydroxy-4a,8-dimethyloctahydronaphthalen-2(1H)-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:

(1R,4S,4aS,8aS)-4-(tert-Butyl-dimethyl-silanyloxy)-7,7-dimethoxy-1,4a-dimethyl-decahydro-naphthalen-1-ol (144494-49-5) → (4aα,5α,8α,8aβ)-5-<(tert-Butyldimethylsilyl)oxy>octahydro-8-hydroxy-4a,8-dimethyl-2(1H)-naphthalenone (136379-65-2)

Guidance literature:

With hydrogenchloride; In water; acetone; for 0.333333h; Yield given; Ambient temperature;

DOI:10.1021/jo00023a025

Reference yield:

4β-Hydroxy-4aβ-methyl-3,4,4a,5,6,8aα-hexahydronaphthalene-1(2H),7(8H)-dione 7-dimethyl acetal (87262-05-3) → (4aα,5α,8α,8aβ)-5-<(tert-Butyldimethylsilyl)oxy>octahydro-8-hydroxy-4a,8-dimethyl-2(1H)-naphthalenone (136379-65-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / imidazole / dimethylformamide / 72 h / Ambient temperature

2: diethyl ether / 42 h / Ambient temperature

3: conc. HCl / acetone; H₂O / 0.33 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; In diethyl ether; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00023a025

Reference yield:

(4α,4aα,8aβ)-4-[(tert-Butyldimethylsilyl)oxy]octahydro-7,7-dimethoxy-4a-methyl-1(2H)-naphthalenone (136379-64-1) → (4aα,5α,8α,8aβ)-5-<(tert-Butyldimethylsilyl)oxy>octahydro-8-hydroxy-4a,8-dimethyl-2(1H)-naphthalenone (136379-65-2)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether / 42 h / Ambient temperature

2: conc. HCl / acetone; H₂O / 0.33 h / Ambient temperature

With hydrogenchloride; In diethyl ether; water; acetone;

DOI:10.1021/jo00023a025

upstream raw materials:

(1R,4S,4aS,8aS)-4-(tert-Butyl-dimethyl-silanyloxy)-7,7-dimethoxy-1,4a-dimethyl-decahydro-naphthalen-1-ol

4β-Hydroxy-4aβ-methyl-3,4,4a,5,6,8aα-hexahydronaphthalene-1(2H),7(8H)-dione 7-dimethyl acetal

(4α,4aα,8aβ)-4-[(tert-Butyldimethylsilyl)oxy]octahydro-7,7-dimethoxy-4a-methyl-1(2H)-naphthalenone

tert-butyldimethylsilyl chloride

Downstream raw materials:

(1aα,3aα,4α,7α,7aβ,7bα)-1,1-Dibromo-4-<(tert-butyldimethylsilyl)oxy>decahydro-3a,7-dimethyl-1H-cyclopropanaphthalen-7-ol

(2aS,3R,6S,6aS)-1,1-Dibromo-6-(tert-butyl-dimethyl-silanyloxy)-3,6a-dimethyl-decahydro-cyclopropa[b]naphthalen-3-ol

(1α,4α,4aα,7β,8aβ)-4-<(tert-Butyldimethylsilyl)oxy>decahydro-1,4a-dimethyl-1,7-naphthalenediol

(1α,4α,4aα,7α,8aβ)-4-<(tert-Butyldimethylsilyl)oxy>decahydro-1,4a-dimethyl-1,7-naphthalenediol