3-[(2S,3S,4R,5R)-3-hydroxy-5-methyl-4-phenylselanyl-5-propyloxolan-2-yl]propanenitrile

Base Information

Chemical Name:3-[(2S,3S,4R,5R)-3-hydroxy-5-methyl-4-phenylselanyl-5-propyloxolan-2-yl]propanenitrile
CAS No.:935761-64-1
Molecular Formula:C₁₇H₂₃NO₂Se
Molecular Weight:352.335
Hs Code.:

Synonyms:3-[(2S,3S,4R,5R)-3-hydroxy-5-methyl-4-phenylselanyl-5-propyloxolan-2-yl]propanenitrile

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Chemical Property of 3-[(2S,3S,4R,5R)-3-hydroxy-5-methyl-4-phenylselanyl-5-propyloxolan-2-yl]propanenitrile

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Technology Process of 3-[(2S,3S,4R,5R)-3-hydroxy-5-methyl-4-phenylselanyl-5-propyloxolan-2-yl]propanenitrile

There total 6 articles about 3-[(2S,3S,4R,5R)-3-hydroxy-5-methyl-4-phenylselanyl-5-propyloxolan-2-yl]propanenitrile 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: 92.0%

: 935761-58-3
(4S,5R,6Z)-4,5-dihydroxy-7-methyl-6-decenenitrile

: 5707-04-0
Phenylselenyl chloride

: 3-[(2S,3S,4S,5S)-3-hydroxy-5-methyl-4-phenylselanyl-5-propyloxolan-2-yl]propanenitrile

: 935761-64-1
3-[(2S,3S,4R,5R)-3-hydroxy-5-methyl-4-phenylselanyl-5-propyloxolan-2-yl]propanenitrile

Guidance literature:: With potassium carbonate; In tetrahydrofuran; at -78 ℃; for 6h;
DOI:10.1021/ol063035y

Reference yield:

: 2-(tert-butyl-dimethyl-silanyloxy)-4-cyano-thiobutyric acid S-dodecyl ester

: 935761-64-1
3-[(2S,3S,4R,5R)-3-hydroxy-5-methyl-4-phenylselanyl-5-propyloxolan-2-yl]propanenitrile

Guidance literature:: Multi-step reaction with 4 steps

1.1: Et₃SiH / Pd/C / CH₂Cl₂ / 0.67 h / 20 °C

2.1: tBuLi / diethyl ether / 0.25 h / -78 °C

2.2: ZnI₂ / diethyl ether / 1 h / -78 - 0 °C

2.3: (-)-N-Me-ephedrine; BuLi / toluene / 14 h / 0 °C

3.1: 94 percent / TBAF*3H₂O / tetrahydrofuran / 1 h / 20 °C

4.1: 60 percent / ZnBr₂ / tetrahydrofuran / 0.25 h / 20 °C

With triethylsilane; tetrabutyl ammonium fluoride; tert.-butyl lithium; zinc dibromide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ol063035y

Reference yield:

: 935761-60-7
5-(4-benzyl-2-oxo-oxazolidin-3-yl)-4-(tert-butyl-dimethyl-silanyloxy)-5-oxo-pentanenitrile

: 935761-64-1
3-[(2S,3S,4R,5R)-3-hydroxy-5-methyl-4-phenylselanyl-5-propyloxolan-2-yl]propanenitrile

Guidance literature:: Multi-step reaction with 5 steps

1.1: BuLi / tetrahydrofuran / 1 h / 0 - 20 °C

2.1: Et₃SiH / Pd/C / CH₂Cl₂ / 0.67 h / 20 °C

3.1: tBuLi / diethyl ether / 0.25 h / -78 °C

3.2: ZnI₂ / diethyl ether / 1 h / -78 - 0 °C

3.3: (-)-N-Me-ephedrine; BuLi / toluene / 14 h / 0 °C

4.1: 94 percent / TBAF*3H₂O / tetrahydrofuran / 1 h / 20 °C

5.1: 60 percent / ZnBr₂ / tetrahydrofuran / 0.25 h / 20 °C

With triethylsilane; n-butyllithium; tetrabutyl ammonium fluoride; tert.-butyl lithium; zinc dibromide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ol063035y