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

Base Information

Chemical Name:(S)-3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-methylene-tetrahydro-furan-2-yl]-butyric acid methyl ester
CAS No.:713122-65-7
Molecular Formula:C₂₇H₃₆O₄Si
Molecular Weight:452.666
Hs Code.:

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

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

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

There total 9 articles about (S)-3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-methylene-tetrahydro-furan-2-yl]-butyric acid methyl ester 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: 67.0%

: bis<(bromozincio)methylene>zinc

: 713122-76-0
(S)-3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-oxo-tetrahydro-furan-2-yl]-butyric acid methyl ester

: 713122-65-7
(S)-3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-methylene-tetrahydro-furan-2-yl]-butyric acid methyl ester

Guidance literature:: With titanium tetrachloride; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃;
DOI:10.1021/ol049483s

Reference yield:

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

: 713122-65-7
(S)-3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-methylene-tetrahydro-furan-2-yl]-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 9 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

8.1: 99 percent / diethyl ether / 1 h / 20 °C

9.1: 67 percent / titanium(IV) chloride / CH₂Cl₂; tetrahydrofuran / 0 - 20 °C

With copper acetylacetonate; dipyridinium dichromate; oxalyl dichloride; trifluorormethanesulfonic acid; bis(cyclohexanyl)borane; potassium trimethylsilonate; titanium tetrachloride; 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

: 713122-65-7
(S)-3-[(2R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-methylene-tetrahydro-furan-2-yl]-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 6 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

5.1: 99 percent / diethyl ether / 1 h / 20 °C

6.1: 67 percent / titanium(IV) chloride / CH₂Cl₂; tetrahydrofuran / 0 - 20 °C

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