(+)-<2R,6S,S(R)>-6-(tert-Butyldimethylsilyloxy)-1-(p-tolylsulfinyl)-heptan-2-ol

Base Information

Chemical Name:(+)-<2R,6S,S(R)>-6-(tert-Butyldimethylsilyloxy)-1-(p-tolylsulfinyl)-heptan-2-ol
CAS No.:158930-52-0
Molecular Formula:C₂₀H₃₆O₃SSi
Molecular Weight:384.656
Hs Code.:

Synonyms:(+)-<2R,6S,S(R)>-6-(tert-Butyldimethylsilyloxy)-1-(p-tolylsulfinyl)-heptan-2-ol

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Chemical Property of (+)-<2R,6S,S(R)>-6-(tert-Butyldimethylsilyloxy)-1-(p-tolylsulfinyl)-heptan-2-ol

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Technology Process of (+)-<2R,6S,S(R)>-6-(tert-Butyldimethylsilyloxy)-1-(p-tolylsulfinyl)-heptan-2-ol

There total 11 articles about (+)-<2R,6S,S(R)>-6-(tert-Butyldimethylsilyloxy)-1-(p-tolylsulfinyl)-heptan-2-ol 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: 79.5%

: 158833-98-8
(+)-<6S,S(R)>-6-(tert-Butyldimethylsilyloxy)-1-(p-tolylsulfinyl)-heptan-2-one

: 158930-52-0
(+)-<2R,6S,S(R)>-6-(tert-Butyldimethylsilyloxy)-1-(p-tolylsulfinyl)-heptan-2-ol

Guidance literature:: With diisobutylaluminium hydride; zinc dibromide; In tetrahydrofuran; toluene; for 0.75h;
DOI:10.1002/recl.19951140405

Reference yield:

: 127953-97-3
(+)-methyl (5S)-5-<(tert-butyldimethylsilyl)oxy>hexanoate

: 158930-52-0
(+)-<2R,6S,S(R)>-6-(tert-Butyldimethylsilyloxy)-1-(p-tolylsulfinyl)-heptan-2-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / LDA / tetrahydrofuran

2: ZnCl₂, DIBAL / -78 °C

With diisobutylaluminium hydride; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran;
DOI:10.1016/S0040-4039(00)77089-4

Reference yield:

: 799247-36-2
(S)-5-oxo-6-(p-toluenesulfinyl)hexanoic acid

: 158930-52-0
(+)-<2R,6S,S(R)>-6-(tert-Butyldimethylsilyloxy)-1-(p-tolylsulfinyl)-heptan-2-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium carbonate / acetone / Reflux

2.1: zinc dibromide / tetrahydrofuran / Reflux

3.1: 1H-imidazole / N,N-dimethyl-formamide / Reflux; Inert atmosphere

3.2: Raney nickel

4.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 - -30 °C / Inert atmosphere; Reflux

4.2: -78 °C

5.1: zinc dibromide; diisobutylaluminium hydride / tetrahydrofuran / -78 °C

With 1H-imidazole; diisobutylaluminium hydride; potassium carbonate; zinc dibromide; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;