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

Base Information

Chemical Name:(+)-(2S,3aS,6aS)-2-(tert-butyldiphenylsilanyloxy)-5-(trimethylsilanyloxy)-1,2,3,3a,4,6a-hexahydropentalene
CAS No.:597557-42-1
Molecular Formula:C₂₇H₃₈O₂Si₂
Molecular Weight:450.769
Hs Code.:

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

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Chemical Property of (+)-(2S,3aS,6aS)-2-(tert-butyldiphenylsilanyloxy)-5-(trimethylsilanyloxy)-1,2,3,3a,4,6a-hexahydropentalene

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Technology Process of (+)-(2S,3aS,6aS)-2-(tert-butyldiphenylsilanyloxy)-5-(trimethylsilanyloxy)-1,2,3,3a,4,6a-hexahydropentalene

There total 1 articles about (+)-(2S,3aS,6aS)-2-(tert-butyldiphenylsilanyloxy)-5-(trimethylsilanyloxy)-1,2,3,3a,4,6a-hexahydropentalene 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:

: 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: 75.0%

: 75-87-6
chloral

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

: 597557-43-2
(1S,3aS,6aS,5S)-5-(tert-butyldiphenylsilanyloxy)-1-(2,2,2-trichloro-1-hydroxyethyl)-hexahydropentalen-2-one

Guidance literature:: chloral; With titanium tetrachloride; In dichloromethane; at 20 ℃; for 0.0833333h;

(+)-(2S,3aS,6aS)-2-(tert-butyldiphenylsilanyloxy)-5-(trimethylsilanyloxy)-1,2,3,3a,4,6a-hexahydropentalene; In dichloromethane; at -78 ℃; for 1h;
DOI:10.1021/ja030200l

Reference yield:

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

: 1-[5-(tert-butyldiphenylsilanyloxy)-2-(triethylsilanyloxy)octahydropentalen-1-yl]-(4S)-methylnona-1,6-diyn-3-one

Guidance literature:: Multi-step reaction with 6 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

6.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 - 20 °C

6.2: tetrahydrofuran; hexane / 3 h / -19 °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