(S)-acetoxyphenylacetic acid (R)-1-[5-(triethylsilyl)furan-3-yl]but-3-ynyl ester

Base Information

Chemical Name:(S)-acetoxyphenylacetic acid (R)-1-[5-(triethylsilyl)furan-3-yl]but-3-ynyl ester
CAS No.:539802-64-7
Molecular Formula:C₂₄H₃₀O₅Si
Molecular Weight:426.585
Hs Code.:

Synonyms:(S)-acetoxyphenylacetic acid (R)-1-[5-(triethylsilyl)furan-3-yl]but-3-ynyl ester

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Chemical Property of (S)-acetoxyphenylacetic acid (R)-1-[5-(triethylsilyl)furan-3-yl]but-3-ynyl ester

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Technology Process of (S)-acetoxyphenylacetic acid (R)-1-[5-(triethylsilyl)furan-3-yl]but-3-ynyl ester

There total 4 articles about (S)-acetoxyphenylacetic acid (R)-1-[5-(triethylsilyl)furan-3-yl]but-3-ynyl 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: 41.0%

: 7322-88-5
(S)-acetylmandelic acid

: 191938-99-5
(RS)-1-(5-triethylsilylfuran-3-yl)-but-3-yn-1-ol

: (S)-acetoxyphenylacetic acid (S)-1-[5-(triethylsilyl)furan-3-yl]but-3-ynyl ester

: 539802-64-7
(S)-acetoxyphenylacetic acid (R)-1-[5-(triethylsilyl)furan-3-yl]but-3-ynyl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at -10 - 0 ℃; for 3h;
DOI:10.1021/jo0268097

Reference yield:

: 498-60-2
furan-3-carboxaldehyde

: 539802-64-7
(S)-acetoxyphenylacetic acid (R)-1-[5-(triethylsilyl)furan-3-yl]but-3-ynyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium morpholide / tetrahydrofuran / -78 °C

1.2: s-BuLi / tetrahydrofuran

1.3: 73 percent / tetrahydrofuran

2.1: Mg; HgCl₂ / diethyl ether; toluene / 1.17 h / -20 - 20 °C

2.2: 91 percent / diethyl ether; toluene / 3 h / -40 - 20 °C

3.1: 41 percent / DCC; DMAP / CH₂Cl₂ / 3 h / -10 - 0 °C

With lithium morpholide; dmap; magnesium; dicyclohexyl-carbodiimide; mercury dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/jo0268097

Reference yield:

: 994-30-9
triethylsilyl chloride

: 539802-64-7
(S)-acetoxyphenylacetic acid (R)-1-[5-(triethylsilyl)furan-3-yl]but-3-ynyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium morpholide / tetrahydrofuran / -78 °C

1.2: s-BuLi / tetrahydrofuran

1.3: 73 percent / tetrahydrofuran

2.1: Mg; HgCl₂ / diethyl ether; toluene / 1.17 h / -20 - 20 °C

2.2: 91 percent / diethyl ether; toluene / 3 h / -40 - 20 °C

3.1: 41 percent / DCC; DMAP / CH₂Cl₂ / 3 h / -10 - 0 °C

With lithium morpholide; dmap; magnesium; dicyclohexyl-carbodiimide; mercury dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/jo0268097