(S)-3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-oxo-tetrahydro-furan-2-yl]-butyric acid

Base Information

Chemical Name:(S)-3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-oxo-tetrahydro-furan-2-yl]-butyric acid
CAS No.:713122-64-6
Molecular Formula:C₂₅H₃₂O₅Si
Molecular Weight:440.612
Hs Code.:

Synonyms:(S)-3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-oxo-tetrahydro-furan-2-yl]-butyric acid

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Chemical Property of (S)-3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-oxo-tetrahydro-furan-2-yl]-butyric acid

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Technology Process of (S)-3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-oxo-tetrahydro-furan-2-yl]-butyric acid

There total 7 articles about (S)-3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-oxo-tetrahydro-furan-2-yl]-butyric acid 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: 74.0%

: (2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-((S)-3-hydroxy-1-methyl-propyl)-tetrahydro-furan-3-ol

: 713122-64-6
(S)-3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-oxo-tetrahydro-furan-2-yl]-butyric acid

Guidance literature:: With dipyridinium dichromate; In N,N-dimethyl-formamide; at 20 ℃; for 48h;
DOI:10.1021/ol049483s

Reference yield:

: 124655-05-6
(S)-methyl 4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate

: 713122-64-6
(S)-3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-oxo-tetrahydro-furan-2-yl]-butyric acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: 60 percent / CF₃SO₃H / CH₂Cl₂ / 20 °C

2.1: 86 percent / potassium trimethylsilanolate / diethyl ether / 20 °C

3.1: oxalyl chloride; dimethylformamide / CH₂Cl₂ / 20 °C

4.1: diethyl ether / 0 - 20 °C

5.1: 88 percent / copper(II) acetylacetonate / tetrahydrofuran / 0.5 h / Heating

6.1: dicyclohexylborane / tetrahydrofuran / 3 h / 0 - 20 °C

6.2: 86 percent / H₂O₂ / tetrahydrofuran; methanol / pH 7

7.1: 74 percent / pyridinium dichromate / dimethylformamide / 48 h / 20 °C

With copper acetylacetonate; dipyridinium dichromate; oxalyl dichloride; trifluorormethanesulfonic acid; bis(cyclohexanyl)borane; potassium trimethylsilonate; N,N-dimethyl-formamide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol049483s

Reference yield:

: (S)-3-[((E)-But-2-enyl)oxy]-4-(tert-butyl-diphenyl-silanyloxy)-butyryl chloride

: 713122-64-6
(S)-3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-oxo-tetrahydro-furan-2-yl]-butyric acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: diethyl ether / 0 - 20 °C

2.1: 88 percent / copper(II) acetylacetonate / tetrahydrofuran / 0.5 h / Heating

3.1: dicyclohexylborane / tetrahydrofuran / 3 h / 0 - 20 °C

3.2: 86 percent / H₂O₂ / tetrahydrofuran; methanol / pH 7

4.1: 74 percent / pyridinium dichromate / dimethylformamide / 48 h / 20 °C

With copper acetylacetonate; dipyridinium dichromate; bis(cyclohexanyl)borane; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/ol049483s