(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-6-(3-phenylselanyl-propyl)-tetrahydro-pyran-2-carbonitrile

Base Information

Chemical Name:(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-6-(3-phenylselanyl-propyl)-tetrahydro-pyran-2-carbonitrile
CAS No.:218965-78-7
Molecular Formula:C₂₃H₃₇NO₂SeSi
Molecular Weight:466.598
Hs Code.:

Synonyms:(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-6-(3-phenylselanyl-propyl)-tetrahydro-pyran-2-carbonitrile

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Chemical Property of (2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-6-(3-phenylselanyl-propyl)-tetrahydro-pyran-2-carbonitrile

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Technology Process of (2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-6-(3-phenylselanyl-propyl)-tetrahydro-pyran-2-carbonitrile

There total 3 articles about (2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-6-(3-phenylselanyl-propyl)-tetrahydro-pyran-2-carbonitrile 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: 91.0%

: 1666-13-3
diphenyl diselenide

: 218965-77-6
(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(3-chloro-propyl)-5,5-dimethyl-tetrahydro-pyran-2-carbonitrile

: 218965-78-7
(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-6-(3-phenylselanyl-propyl)-tetrahydro-pyran-2-carbonitrile

Guidance literature:: With sodium tetrahydroborate; In ethanol; for 1h; Heating;
DOI:10.1055/s-1998-1970

Reference yield:

: 210691-79-5
(R)-6-(3-Chloropropyl)-5,6-dihydro-5,5-dimethyl-4H-pyran-4-one

: 218965-78-7
(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-6-(3-phenylselanyl-propyl)-tetrahydro-pyran-2-carbonitrile

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / TMSOTf / CH₂Cl₂ / 1.5 h / 0 °C

2: NaBH₄, CeCl₃*7H₂O / methanol / 1.5 h / -90 - -30 °C

3: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2.5 h / 0 °C

4: 91 percent / NaBH₄ / ethanol / 1 h / Heating

With 2,6-dimethylpyridine; sodium tetrahydroborate; cerium(III) chloride; trimethylsilyl trifluoromethanesulfonate; In methanol; ethanol; dichloromethane;
DOI:10.1055/s-1998-1970

Reference yield:

: 218965-76-5
(2S,4R,6R)-6-(3-Chloropropyl)-2-cyanotetrahydro-5,5-dimethyl-2H-pyran-4-ol

: 218965-78-7
(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-5,5-dimethyl-6-(3-phenylselanyl-propyl)-tetrahydro-pyran-2-carbonitrile

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 2.5 h / 0 °C

2: 91 percent / NaBH₄ / ethanol / 1 h / Heating

With 2,6-dimethylpyridine; sodium tetrahydroborate; In ethanol; dichloromethane;
DOI:10.1055/s-1998-1970