(1R,4S,4aS,8aS)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,4a-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol

Base Information

Chemical Name:(1R,4S,4aS,8aS)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,4a-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol
CAS No.:136379-62-9
Molecular Formula:C₁₈H₃₄O₂Si
Molecular Weight:310.552
Hs Code.:

Synonyms:1-Naphthalenol,4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,2,3,4,4a,5,6,8a-octahydro-1,4a-dimethyl-,(1a,4a,4aa,8ab)- (9CI); 1-Naphthalenol,4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,2,3,4,4a,5,6,8a-octahydro-1,4a-dimethyl-,(1a,4a,4aa,8ab)-(?à)-

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Chemical Property of (1R,4S,4aS,8aS)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,4a-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol

Chemical Property:

Vapor Pressure:3.01E-06mmHg at 25°C
Boiling Point:348.7°C at 760 mmHg
Flash Point:164.7°C
Density:0.96g/cm³

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (1R,4S,4aS,8aS)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,4a-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol

There total 8 articles about (1R,4S,4aS,8aS)-4-{[tert-butyl(dimethyl)silyl]oxy}-1,4a-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-ol 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: 54.0%

: 136379-68-5
(1α,4α,4aα,7α,8aβ)-5-<(tert-butyldimethylsilyl)oxy>decahydro-1,4a-dimethyl-1,7-naphthalene-diol 7-(methanesulfonate)

: 136379-62-9
(1α,4α,4aα,8aβ)-4-<(tert-Butyldimethylsilyl)oxy>-1,2,3,4,4a,5,6,8a-octahydro-1,4a-dimethyl-1-naphthalenol

: 136379-69-6
(1α,4α,4aα,8aβ)-4-<(tert-Butyldimethylsilyl)oxy>-1,2,3,4,4a,5,8,8a-octahydro-1,4a-dimethyl-1-naphthalenol

: 5(R*)-<(tert-butyldimethylsilyl)oxy>-5-<(1'α,2'α,5'α)-2'-methylbicyclo<3.1.0>hexan-2'-yl>pentan-2-one

Guidance literature:: With 15-crown-5; sodium tert-pentoxide; In toluene; benzene; for 0.166667h; Yields of byproduct given; Heating;
DOI:10.1021/jo00057a037

Reference yield:

: 136379-61-8
(1α,4α,4aα,7β,8aβ)-5-<(tert-butyldimethylsilyl)oxy>decahydro-1,4a-dimethyl-1,7-naphthalene-diol 7-(methanesulfonate)

: 136379-62-9
(1α,4α,4aα,8aβ)-4-<(tert-Butyldimethylsilyl)oxy>-1,2,3,4,4a,5,6,8a-octahydro-1,4a-dimethyl-1-naphthalenol

: 136379-69-6
(1α,4α,4aα,8aβ)-4-<(tert-Butyldimethylsilyl)oxy>-1,2,3,4,4a,5,8,8a-octahydro-1,4a-dimethyl-1-naphthalenol

Guidance literature:: With sodium tert-pentoxide; In toluene; for 0.166667h; Yields of byproduct given; Heating;
DOI:10.1021/jo00023a025

Reference yield:

: 87262-05-3
4β-Hydroxy-4aβ-methyl-3,4,4a,5,6,8aα-hexahydronaphthalene-1(2H),7(8H)-dione 7-dimethyl acetal

: 136379-62-9
(1α,4α,4aα,8aβ)-4-<(tert-Butyldimethylsilyl)oxy>-1,2,3,4,4a,5,6,8a-octahydro-1,4a-dimethyl-1-naphthalenol

Guidance literature:: Multi-step reaction with 5 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

4: 1.) L-Selectride, 2.) pyridine / 1.) THF, -78 to 0 deg C over 1 h, 2.) 40 deg C, 2 h

5: sodium tert-amylate / toluene / 0.17 h / Heating

With pyridine; 1H-imidazole; hydrogenchloride; sodium tert-pentoxide; L-Selectride; In diethyl ether; water; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/jo00023a025