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

Base Information

Chemical Name:5(S)-[1(S)-[(tert-butyldimethylsilyl)oxy]-2-phenylethyl]dihydrofuran-2(3H)-one
CAS No.:220588-83-0
Molecular Formula:C₁₈H₂₈O₃Si
Molecular Weight:320.504
Hs Code.:

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

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

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

There total 8 articles about 5(S)-[1(S)-[(tert-butyldimethylsilyl)oxy]-2-phenylethyl]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: 87.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 125225-52-7
(5S,1'S)-5-(1'-hydroxy-2'-phenylethyl)dihydrofuran-2(3H)-one

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

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 - 25 ℃; for 0.75h;
DOI:10.1016/S0968-0896(98)80011-4

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 8 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

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; jones' reagent; oxalyl dichloride; hydrogen; sodium hydride; ozone; dimethyl sulfoxide; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; 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;
DOI:10.1016/S0968-0896(98)80011-4

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

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