(-)-(1R,5S,6S)-6-(tert-butyldimethylsilyloxymethyl)bicyclo[3.1.0]hex-2-en-3-yl triflate

Base Information

Chemical Name:(-)-(1R,5S,6S)-6-(tert-butyldimethylsilyloxymethyl)bicyclo[3.1.0]hex-2-en-3-yl triflate
CAS No.:497839-39-1
Molecular Formula:C₂₄H₂₇F₃O₄SSi
Molecular Weight:496.623
Hs Code.:

Synonyms:(-)-(1R,5S,6S)-6-(tert-butyldimethylsilyloxymethyl)bicyclo[3.1.0]hex-2-en-3-yl triflate

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Chemical Property of (-)-(1R,5S,6S)-6-(tert-butyldimethylsilyloxymethyl)bicyclo[3.1.0]hex-2-en-3-yl triflate

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Technology Process of (-)-(1R,5S,6S)-6-(tert-butyldimethylsilyloxymethyl)bicyclo[3.1.0]hex-2-en-3-yl triflate

There total 4 articles about (-)-(1R,5S,6S)-6-(tert-butyldimethylsilyloxymethyl)bicyclo[3.1.0]hex-2-en-3-yl triflate 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:

: 145100-51-2
N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide

: 6α-(tert-butyldiphenylsilyloxymethyl)-1α,5α-bicyclo[3.1.0]hexan-3-one

: 497839-39-1
(-)-(1R,5S,6S)-6-(tert-butyldimethylsilyloxymethyl)bicyclo[3.1.0]hex-2-en-3-yl triflate

: 497839-38-0
(+)-(1S,5R,6R)-6-(tert-butyldimethylsilyloxymethyl)bicyclo[3.1.0]hex-2-en-3-yl triflate

Guidance literature:: 6α-(tert-butyldiphenylsilyloxymethyl)-1α,5α-bicyclo[3.1.0]hexan-3-one; With n-butyllithium; (R)-N-(2,2,2-trifluoroethyl)-1-phenylethylamine hydrochloride; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h; Title compound not separated from byproducts;
DOI:10.1016/S0957-4166(02)00405-6

Reference yield:

: 1713-75-3,29569-85-5,54561-38-5,69169-18-2
endo-6-hydroxymethylbicyclo<3.1.0>hex-2-ene

: 497839-39-1
(-)-(1R,5S,6S)-6-(tert-butyldimethylsilyloxymethyl)bicyclo[3.1.0]hex-2-en-3-yl triflate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 88 percent / imidazole / dimethylformamide / 0.5 h / 20 °C

2.1: NH₃*SMe₂ / tetrahydrofuran / 0.75 h / 20 °C

2.2: aq. naOH; aq. H₂O₂ / methanol / 1 h / Heating

2.3: 51 percent / PDC; HYFLO SUPER GEL(R) / CH₂Cl₂ / 15 h / 20 °C

3.1: n-BuLi; (S,S)-bis(α-methylbenzyl)amine hydrochloride / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: tetrahydrofuran; hexane / 1.5 h / -78 °C

With 1H-imidazole; n-butyllithium; ammonia, dimethyl sulfide; hydrochloride salt of (1S,1'S)-bis(1-phenylethyl)amine; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;
DOI:10.1016/S0957-4166(02)00405-6

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 497839-39-1
(-)-(1R,5S,6S)-6-(tert-butyldimethylsilyloxymethyl)bicyclo[3.1.0]hex-2-en-3-yl triflate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 88 percent / imidazole / dimethylformamide / 0.5 h / 20 °C

2.1: NH₃*SMe₂ / tetrahydrofuran / 0.75 h / 20 °C

2.2: aq. naOH; aq. H₂O₂ / methanol / 1 h / Heating

2.3: 51 percent / PDC; HYFLO SUPER GEL(R) / CH₂Cl₂ / 15 h / 20 °C

3.1: n-BuLi; (S,S)-bis(α-methylbenzyl)amine hydrochloride / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: tetrahydrofuran; hexane / 1.5 h / -78 °C

With 1H-imidazole; n-butyllithium; ammonia, dimethyl sulfide; hydrochloride salt of (1S,1'S)-bis(1-phenylethyl)amine; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;
DOI:10.1016/S0957-4166(02)00405-6