(2RS,4S,5R)-4-(tert-butyldimethylsilyloxy)-2-phenylsulfinyl-5-(2-triethylsilyloxyethyl)cyclohexanone

Base Information

Chemical Name:(2RS,4S,5R)-4-(tert-butyldimethylsilyloxy)-2-phenylsulfinyl-5-(2-triethylsilyloxyethyl)cyclohexanone
CAS No.:882494-41-9
Molecular Formula:C₂₆H₄₆O₄SSi₂
Molecular Weight:510.886
Hs Code.:

Synonyms:

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Chemical Property of (2RS,4S,5R)-4-(tert-butyldimethylsilyloxy)-2-phenylsulfinyl-5-(2-triethylsilyloxyethyl)cyclohexanone

Chemical Property:

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Technology Process of (2RS,4S,5R)-4-(tert-butyldimethylsilyloxy)-2-phenylsulfinyl-5-(2-triethylsilyloxyethyl)cyclohexanone

There total 10 articles about (2RS,4S,5R)-4-(tert-butyldimethylsilyloxy)-2-phenylsulfinyl-5-(2-triethylsilyloxyethyl)cyclohexanone 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:

: 882494-40-8
(3R,4S)-4-(tert-butyldimethylsilyloxy)-3-(2-triethylsilyloxyethyl)cyclohexanone

: 1212-08-4
S-Phenyl benzenethiosulfonate

: (3S,4S)-2-Benzenesulfinyl-4-(tert-butyl-dimethyl-silanyloxy)-3-(2-triethylsilanyloxy-ethyl)-cyclohexanone

: 882494-41-9
(2RS,4S,5R)-4-(tert-butyldimethylsilyloxy)-2-phenylsulfinyl-5-(2-triethylsilyloxyethyl)cyclohexanone

Guidance literature:: (3R,4S)-4-(tert-butyldimethylsilyloxy)-3-(2-triethylsilyloxyethyl)cyclohexanone; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.05h;

S-Phenyl benzenethiosulfonate; In tetrahydrofuran; at -78 ℃; for 1h;

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 1h;
DOI:10.1016/j.tet.2005.12.009

Reference yield:

: 882494-39-5
(3R,4S)-4-(tert-butyldimethylsilyloxy)-3-(2-hydroxyethyl)cyclohexanone

: 882494-41-9
(2RS,4S,5R)-4-(tert-butyldimethylsilyloxy)-2-phenylsulfinyl-5-(2-triethylsilyloxyethyl)cyclohexanone

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1.23 g / triethylamine / CH₂Cl₂ / 0.75 h / 20 °C

2.1: lithium diisopropylamide / tetrahydrofuran / 0.05 h / -78 °C

2.2: tetrahydrofuran / 1 h / -78 °C

2.3: 1.53 g / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / -78 °C

With triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2005.12.009

Reference yield:

: 882494-34-0
[(1R,2S)-5,5-ethylenedioxy-2-(tert-butyldimethylsilyloxy)cyclohexyl]methanol

: 882494-41-9
(2RS,4S,5R)-4-(tert-butyldimethylsilyloxy)-2-phenylsulfinyl-5-(2-triethylsilyloxyethyl)cyclohexanone

Guidance literature:: Multi-step reaction with 7 steps

1.1: 89 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / 20 °C

2.1: 93 percent / dimethylsulfoxide / 4 h / 100 °C

3.1: 94 percent / DIBAL / CH₂Cl₂ / 2.5 h / -78 °C

4.1: 99 percent / sodium borohydride / ethanol / -20 - 0 °C

5.1: 0.86 g / p-toluenesulfonic acid monohydrate / acetone / 48 h / 20 °C

6.1: 1.23 g / triethylamine / CH₂Cl₂ / 0.75 h / 20 °C

7.1: lithium diisopropylamide / tetrahydrofuran / 0.05 h / -78 °C

7.2: tetrahydrofuran / 1 h / -78 °C

7.3: 1.53 g / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / -78 °C

With dmap; sodium tetrahydroborate; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; acetone;
DOI:10.1016/j.tet.2005.12.009