(-)-(1S,2R,3aR,5S,6aS)-5-(tert-butyldiphenylsilanyloxy)-1-ethynyl-2-(triethylsilanyloxy)octahydropentalene

Base Information

Chemical Name:(-)-(1S,2R,3aR,5S,6aS)-5-(tert-butyldiphenylsilanyloxy)-1-ethynyl-2-(triethylsilanyloxy)octahydropentalene
CAS No.:597557-40-9
Molecular Formula:C₃₂H₄₆O₂Si₂
Molecular Weight:518.887
Hs Code.:

Synonyms:(-)-(1S,2R,3aR,5S,6aS)-5-(tert-butyldiphenylsilanyloxy)-1-ethynyl-2-(triethylsilanyloxy)octahydropentalene

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Chemical Property of (-)-(1S,2R,3aR,5S,6aS)-5-(tert-butyldiphenylsilanyloxy)-1-ethynyl-2-(triethylsilanyloxy)octahydropentalene

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Technology Process of (-)-(1S,2R,3aR,5S,6aS)-5-(tert-butyldiphenylsilanyloxy)-1-ethynyl-2-(triethylsilanyloxy)octahydropentalene

There total 6 articles about (-)-(1S,2R,3aR,5S,6aS)-5-(tert-butyldiphenylsilanyloxy)-1-ethynyl-2-(triethylsilanyloxy)octahydropentalene 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,2R,3aR,5S,6aS)-methanesulfonic acid 1-[5-(tert-butyldiphenylsilanyloxy)-2-(triethylsilanyloxy)octahydropentalen-1-yl]-2,2,2-trichloroethyl ester

: 597557-40-9
(-)-(1S,2R,3aR,5S,6aS)-5-(tert-butyldiphenylsilanyloxy)-1-ethynyl-2-(triethylsilanyloxy)octahydropentalene

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at -20 - 20 ℃;
DOI:10.1021/ja030200l

Reference yield:

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

: 597557-40-9
(-)-(1S,2R,3aR,5S,6aS)-5-(tert-butyldiphenylsilanyloxy)-1-ethynyl-2-(triethylsilanyloxy)octahydropentalene

Guidance literature:: Multi-step reaction with 6 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

5.1: DABCO / tetrahydrofuran / 2 h

6.1: n-BuLi / tetrahydrofuran; hexane / -20 - 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; sodium tetrahydroborate; n-butyllithium; 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

Reference yield:

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

: 597557-40-9
(-)-(1S,2R,3aR,5S,6aS)-5-(tert-butyldiphenylsilanyloxy)-1-ethynyl-2-(triethylsilanyloxy)octahydropentalene

Guidance literature:: Multi-step reaction with 5 steps

1.1: TiCl₄ / CH₂Cl₂ / 0.08 h / 20 °C

1.2: 75 percent / CH₂Cl₂ / 1 h / -78 °C

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

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

4.1: DABCO / tetrahydrofuran / 2 h

5.1: n-BuLi / tetrahydrofuran; hexane / -20 - 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 1H-imidazole; sodium tetrahydroborate; n-butyllithium; titanium tetrachloride; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja030200l