(3aS,5S,6aR)-5-(tert-Butyl-diphenyl-silanyloxy)-hexahydro-pentalen-2-one

Base Information

Chemical Name:(3aS,5S,6aR)-5-(tert-Butyl-diphenyl-silanyloxy)-hexahydro-pentalen-2-one
CAS No.:208388-97-0
Molecular Formula:C₂₄H₃₀O₂Si
Molecular Weight:378.587
Hs Code.:

Synonyms:(3aS,5S,6aR)-5-(tert-Butyl-diphenyl-silanyloxy)-hexahydro-pentalen-2-one

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Chemical Property of (3aS,5S,6aR)-5-(tert-Butyl-diphenyl-silanyloxy)-hexahydro-pentalen-2-one

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Technology Process of (3aS,5S,6aR)-5-(tert-Butyl-diphenyl-silanyloxy)-hexahydro-pentalen-2-one

There total 1 articles about (3aS,5S,6aR)-5-(tert-Butyl-diphenyl-silanyloxy)-hexahydro-pentalen-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: 97.0%

: (3'aα,5'β,6'aα)-(1,1-dimethylethyl)-[hexahydro-5,5-dimethylspiro(1,3-dioxane-2,2'(1'H)-pentalen)-5'-yloxy]diphenylsilane

: 208388-97-0
(3aS,5S,6aR)-5-(tert-Butyl-diphenyl-silanyloxy)-hexahydro-pentalen-2-one

Guidance literature:: With water; toluene-4-sulfonic acid; In acetone; for 3h; Ambient temperature;
DOI:10.1002/(SICI)1099-0690(199805)1998:5<805::AID-EJOC805>3.0.CO;2-R

Reference yield:

: 75-77-4
chloro-trimethyl-silane

: 208388-97-0
(3aS,5S,6aR)-5-(tert-Butyl-diphenyl-silanyloxy)-hexahydro-pentalen-2-one

: 597557-42-1
(+)-(2S,3aS,6aS)-2-(tert-butyldiphenylsilanyloxy)-5-(trimethylsilanyloxy)-1,2,3,3a,4,6a-hexahydropentalene

: (-)-(2R,3aR,6aR)-2-(tert-butyldiphenylsilanyloxy)-5-(trimethylsilanyloxy)-1,2,3,3a,4,6a-hexahydropentalene

Guidance literature:: (3aS,5S,6aR)-5-(tert-Butyl-diphenyl-silanyloxy)-hexahydro-pentalen-2-one; With lithium [R(R*,R*)]-(+)-bis(α-methylbenzyl)amide; In tetrahydrofuran; hexane; at -105 ℃; for 0.416667h;

chloro-trimethyl-silane; In tetrahydrofuran; hexane; at -105 - -78 ℃; Title compound not separated from byproducts;
DOI:10.1021/ja030200l

Reference yield:

: 208388-97-0
(3aS,5S,6aR)-5-(tert-Butyl-diphenyl-silanyloxy)-hexahydro-pentalen-2-one

: (1R,2R,3aS,5S,6aS)-5-(tert-Butyl-diphenyl-silanyloxy)-1-(2,2,2-trichloro-1-triethylsilanyloxy-ethyl)-2-triethylsilanyloxy-octahydro-pentalene

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium (R,R)-bis(phenylethyl)amide / tetrahydrofuran; hexane / 0.42 h / -105 °C

1.2: tetrahydrofuran; hexane / -105 - -78 °C

2.1: TiCl₄ / CH₂Cl₂ / 0.08 h / 20 °C

2.2: 75 percent / CH₂Cl₂ / 1 h / -78 °C

3.1: NaBH₄ / diethyl ether; ethanol / 16 h / -45 °C

4.1: imidazole / dimethylformamide / 0.42 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; titanium tetrachloride; lithium [R(R*,R*)]-(+)-bis(α-methylbenzyl)amide; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja030200l