3a-benzenesulfonyl-6a-(tert-butyl-dimethyl-silanyloxymethyl)-1,3a,3b,4,6a,6b-hexahydro-2H-cyclopropa[de]naphthalen-3-one

Base Information

Chemical Name:3a-benzenesulfonyl-6a-(tert-butyl-dimethyl-silanyloxymethyl)-1,3a,3b,4,6a,6b-hexahydro-2H-cyclopropa[de]naphthalen-3-one
CAS No.:637362-52-8
Molecular Formula:C₂₃H₃₂O₄SSi
Molecular Weight:432.656
Hs Code.:

3a-benzenesulfonyl-6a-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-1,3a,3b,4,6a,6b-hexahydro-2<i>H</i>-cyclopropa[<i>de</i>]naphthalen-3-one

Synonyms:3a-benzenesulfonyl-6a-(tert-butyl-dimethyl-silanyloxymethyl)-1,3a,3b,4,6a,6b-hexahydro-2H-cyclopropa[de]naphthalen-3-one

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Chemical Property of 3a-benzenesulfonyl-6a-(tert-butyl-dimethyl-silanyloxymethyl)-1,3a,3b,4,6a,6b-hexahydro-2H-cyclopropa[de]naphthalen-3-one

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Technology Process of 3a-benzenesulfonyl-6a-(tert-butyl-dimethyl-silanyloxymethyl)-1,3a,3b,4,6a,6b-hexahydro-2H-cyclopropa[de]naphthalen-3-one

There total 10 articles about 3a-benzenesulfonyl-6a-(tert-butyl-dimethyl-silanyloxymethyl)-1,3a,3b,4,6a,6b-hexahydro-2H-cyclopropa[de]naphthalen-3-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:

: 637362-51-7
1-benzenesulfonyl-4-[1-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohexa-2,5-dienyl]-1-diazo-butan-2-one

: 637362-52-8
3a-benzenesulfonyl-6a-(tert-butyl-dimethyl-silanyloxymethyl)-1,3a,3b,4,6a,6b-hexahydro-2H-cyclopropa[de]naphthalen-3-one

: 3a-benzenesulfonyl-6a-(tert-butyl-dimethyl-silanyloxymethyl)-1,3a,3b,4,6a,6b-hexahydro-2H-cyclopropa[de]naphthalen-3-one

Guidance literature:: With dimethyl-diisopropyl-bisoxazoline derivative; copper(I) triflate; In toluene; at 20 ℃; for 0.5h;
DOI:10.1016/j.tetlet.2003.09.215

Reference yield:

: 3112-85-4
methylphenylsulfonate

: 637362-52-8
3a-benzenesulfonyl-6a-(tert-butyl-dimethyl-silanyloxymethyl)-1,3a,3b,4,6a,6b-hexahydro-2H-cyclopropa[de]naphthalen-3-one

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / n-BuLi / tetrahydrofuran / 0 °C

2: 90 percent / TsN₃; TEA / acetonitrile / 6 h / 0 - 20 °C

3: dimethyl-diisopropyl-bisoxazoline derivative / CuOTf / toluene / 0.5 h / 20 °C

With n-butyllithium; 4-toluenesulfonyl azide; dimethyl-diisopropyl-bisoxazoline derivative; TEA; copper(I) triflate; In tetrahydrofuran; toluene; acetonitrile;
DOI:10.1016/j.tetlet.2003.09.215

Reference yield:

: 74269-63-9
(1-Benzyloxymethyl-cyclohexa-2,5-dienyl)-methanol

: 637362-52-8
3a-benzenesulfonyl-6a-(tert-butyl-dimethyl-silanyloxymethyl)-1,3a,3b,4,6a,6b-hexahydro-2H-cyclopropa[de]naphthalen-3-one

Guidance literature:: Multi-step reaction with 8 steps

1: 97 percent / imidazole; DMAP / dimethylformamide; CH₂Cl₂ / 10 h / 20 °C

2: 94 percent / Li; liq. NH₃ / tetrahydrofuran / 0.33 h / -20 °C

3: 90 percent / Dess-Martin reagent; NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

4: 99 percent / t-BuOK / tetrahydrofuran / -78 - 0 °C

5: 88 percent / Mg / 0 °C

6: 92 percent / n-BuLi / tetrahydrofuran / 0 °C

7: 90 percent / TsN₃; TEA / acetonitrile / 6 h / 0 - 20 °C

8: dimethyl-diisopropyl-bisoxazoline derivative / CuOTf / toluene / 0.5 h / 20 °C

With 1H-imidazole; dmap; n-butyllithium; 4-toluenesulfonyl azide; dimethyl-diisopropyl-bisoxazoline derivative; TEA; potassium tert-butylate; ammonia; lithium; sodium hydrogencarbonate; Dess-Martin periodane; magnesium; copper(I) triflate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 3: Dess-Martin oxidation / 4: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tetlet.2003.09.215