5(S)-[2-phenyl-1(S)-[(tert-butyldimethylsilyl)oxy]ethyl]-3(S)-(2-thienylmethyl)dihydrofuran-2(3H)-one

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Chemical Name:5(S)-[2-phenyl-1(S)-[(tert-butyldimethylsilyl)oxy]ethyl]-3(S)-(2-thienylmethyl)dihydrofuran-2(3H)-one
CAS No.:220588-84-1
Molecular Formula:C₂₃H₃₂O₃SSi
Molecular Weight:416.657
Hs Code.:

Synonyms:5(S)-[2-phenyl-1(S)-[(tert-butyldimethylsilyl)oxy]ethyl]-3(S)-(2-thienylmethyl)dihydrofuran-2(3H)-one

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Chemical Property of 5(S)-[2-phenyl-1(S)-[(tert-butyldimethylsilyl)oxy]ethyl]-3(S)-(2-thienylmethyl)dihydrofuran-2(3H)-one

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Technology Process of 5(S)-[2-phenyl-1(S)-[(tert-butyldimethylsilyl)oxy]ethyl]-3(S)-(2-thienylmethyl)dihydrofuran-2(3H)-one

There total 10 articles about 5(S)-[2-phenyl-1(S)-[(tert-butyldimethylsilyl)oxy]ethyl]-3(S)-(2-thienylmethyl)dihydrofuran-2(3H)-one 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: 44.0%

: 765-50-4
2-Chloromethylthiophene

: 220588-83-0
5(S)-[1(S)-[(tert-butyldimethylsilyl)oxy]-2-phenylethyl]dihydrofuran-2(3H)-one

: 5(S)-[2-phenyl-1(S)-[(tert-butyldimethylsilyl)oxy]ethyl]-3(R)-(2-thienylmethyl)dihydrofuran-2(3H)-one

: 220588-84-1
5(S)-[2-phenyl-1(S)-[(tert-butyldimethylsilyl)oxy]ethyl]-3(S)-(2-thienylmethyl)dihydrofuran-2(3H)-one

Guidance literature:: 5(S)-[1(S)-[(tert-butyldimethylsilyl)oxy]-2-phenylethyl]dihydrofuran-2(3H)-one; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

2-Chloromethylthiophene; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; hexane; at -78 - -50 ℃; for 3h;
DOI:10.1016/S0968-0896(98)80011-4

Reference yield:

: 20312-36-1
L-3-phenyllactic acid

: 220588-84-1
5(S)-[2-phenyl-1(S)-[(tert-butyldimethylsilyl)oxy]ethyl]-3(S)-(2-thienylmethyl)dihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: NaH / tetrahydrofuran / 168 h

2.1: 16.3 g / LiAlH₄ / tetrahydrofuran / 60 h

3.1: dimethyl sulfoxide; oxalyl chloride; Et₃N / CH₂Cl₂ / 0.83 h / -78 °C

4.1: 4.82 g / diethyl ether / 1.25 h / -78 °C

5.1: O₃ / methanol / -78 °C

5.2: Me₂S / methanol / 4 h / -78 - 25 °C

6.1: 390 mg / Jones' reagent / acetone / 0.25 h / 0 - 20 °C

7.1: 84 percent / H₂ / Pd(OH)2/C / ethanol / 48 h

8.1: 87 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / 0 - 25 °C

9.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

9.2: 44 percent / HMPA / tetrahydrofuran; hexane / 3 h / -78 - -50 °C

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; jones' reagent; oxalyl dichloride; hydrogen; sodium hydride; ozone; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; acetone; 1.1: Alkylation / 2.1: Reduction / 3.1: Swern oxidation / 4.1: Grignard reaction / 5.1: ozonation / 5.2: Reduction / 6.1: Oxidation / 7.1: Hydrogenolysis / 8.1: silylation / 9.1: Metallation / 9.2: Alkylation;
DOI:10.1016/S0968-0896(98)80011-4

Reference yield:

: 118535-75-4
(2S)-2-benzyloxy-3-phenylpropanal

: 220588-84-1
5(S)-[2-phenyl-1(S)-[(tert-butyldimethylsilyl)oxy]ethyl]-3(S)-(2-thienylmethyl)dihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 4.82 g / diethyl ether / 1.25 h / -78 °C

2.1: O₃ / methanol / -78 °C

2.2: Me₂S / methanol / 4 h / -78 - 25 °C

3.1: 390 mg / Jones' reagent / acetone / 0.25 h / 0 - 20 °C

4.1: 84 percent / H₂ / Pd(OH)2/C / ethanol / 48 h

5.1: 87 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / 0 - 25 °C

6.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: 44 percent / HMPA / tetrahydrofuran; hexane / 3 h / -78 - -50 °C

With 2,6-dimethylpyridine; jones' reagent; hydrogen; ozone; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; acetone; 1.1: Grignard reaction / 2.1: ozonation / 2.2: Reduction / 3.1: Oxidation / 4.1: Hydrogenolysis / 5.1: silylation / 6.1: Metallation / 6.2: Alkylation;
DOI:10.1016/S0968-0896(98)80011-4