(1S,4S,4aS,5S,6R,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-6-(2,2-dibromo-vinyl)-4,7-dimethyl-1-triisopropylsilanyloxy-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

Base Information

Chemical Name:(1S,4S,4aS,5S,6R,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-6-(2,2-dibromo-vinyl)-4,7-dimethyl-1-triisopropylsilanyloxy-1,2,3,4,4a,5,6,8a-octahydro-naphthalene
CAS No.:669010-48-4
Molecular Formula:C₄₀H₆₀Br₂O₂Si₂
Molecular Weight:788.894
Hs Code.:

(1S,4S,4aS,5S,6R,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-6-(2,2-dibromo-vinyl)-4,7-dimethyl-1-triisopropylsilanyloxy-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

Synonyms:(1S,4S,4aS,5S,6R,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-6-(2,2-dibromo-vinyl)-4,7-dimethyl-1-triisopropylsilanyloxy-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

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Chemical Property of (1S,4S,4aS,5S,6R,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-6-(2,2-dibromo-vinyl)-4,7-dimethyl-1-triisopropylsilanyloxy-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

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Technology Process of (1S,4S,4aS,5S,6R,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-6-(2,2-dibromo-vinyl)-4,7-dimethyl-1-triisopropylsilanyloxy-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

There total 8 articles about (1S,4S,4aS,5S,6R,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-6-(2,2-dibromo-vinyl)-4,7-dimethyl-1-triisopropylsilanyloxy-1,2,3,4,4a,5,6,8a-octahydro-naphthalene 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: 93.0%

: 558-13-4
carbon tetrabromide

: 669010-47-3
(1S,2S,4aS,5S,8S,8aS)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-3,8-dimethyl-5-triisopropylsilanyloxy-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbaldehyde

: 669010-48-4
(1S,4S,4aS,5S,6R,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-6-(2,2-dibromo-vinyl)-4,7-dimethyl-1-triisopropylsilanyloxy-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

Guidance literature:: With triphenylphosphine; In dichloromethane; at 20 ℃;
DOI:10.1021/ol036338q

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 669010-48-4
(1S,4S,4aS,5S,6R,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-6-(2,2-dibromo-vinyl)-4,7-dimethyl-1-triisopropylsilanyloxy-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / imidazole / CH₂Cl₂ / 20 °C

2: 87 percent / HCl / tetrahydrofuran / 20 °C

3: 78 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

4: 93 percent / PPh₃ / CH₂Cl₂ / 20 °C

With 1H-imidazole; hydrogenchloride; Dess-Martin periodane; triphenylphosphine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol036338q

Reference yield:

: 4,9-dimethyl-6-triisopropylsilanyloxy-3a,5a,6,7,8,9,9a,9b-octahydro-3H-naphtho[1,2-c]furan-1-one

: 669010-48-4
(1S,4S,4aS,5S,6R,8aS)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-6-(2,2-dibromo-vinyl)-4,7-dimethyl-1-triisopropylsilanyloxy-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

Guidance literature:: Multi-step reaction with 7 steps

1: i-PrMgCl / tetrahydrofuran / 0 °C

2: 90 percent / PPTS / CH₂Cl₂ / 20 °C

3: 89 percent / BH₃-NH₃; LDA / tetrahydrofuran / 0 - 20 °C

4: 98 percent / imidazole / CH₂Cl₂ / 20 °C

5: 87 percent / HCl / tetrahydrofuran / 20 °C

6: 78 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

7: 93 percent / PPh₃ / CH₂Cl₂ / 20 °C

With 1H-imidazole; hydrogenchloride; borane-ammonia complex; isopropylmagnesium chloride; pyridinium p-toluenesulfonate; Dess-Martin periodane; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol036338q