Benzoic acid (E)-(S)-2-ethynyl-3-fluoro-2-hydroxy-5-oxo-pent-3-enyl ester

Base Information

Chemical Name:Benzoic acid (E)-(S)-2-ethynyl-3-fluoro-2-hydroxy-5-oxo-pent-3-enyl ester
CAS No.:765311-74-8
Molecular Formula:C₁₄H₁₁FO₄
Molecular Weight:262.237
Hs Code.:

Synonyms:Benzoic acid (E)-(S)-2-ethynyl-3-fluoro-2-hydroxy-5-oxo-pent-3-enyl ester

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Chemical Property of Benzoic acid (E)-(S)-2-ethynyl-3-fluoro-2-hydroxy-5-oxo-pent-3-enyl ester

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Technology Process of Benzoic acid (E)-(S)-2-ethynyl-3-fluoro-2-hydroxy-5-oxo-pent-3-enyl ester

There total 7 articles about Benzoic acid (E)-(S)-2-ethynyl-3-fluoro-2-hydroxy-5-oxo-pent-3-enyl 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: 91.1%

: 765311-72-6
(2S,5R)-1-O-benzoyl-5,6-dihydroxy-3E-fluoro-2-hydroxy-2-ethynyl-3-hexene

: 765311-74-8
Benzoic acid (E)-(S)-2-ethynyl-3-fluoro-2-hydroxy-5-oxo-pent-3-enyl ester

Guidance literature:: With sodium periodate; In ethanol; water; at 20 ℃; for 0.5h;
DOI:10.1021/jo049597h

Reference yield:

: 765311-64-6
(5R)-5-hydroxy-6-(tert-butyldimethylsilyloxy)-3-fluoro-1,3-dihexene

: 765311-74-8
Benzoic acid (E)-(S)-2-ethynyl-3-fluoro-2-hydroxy-5-oxo-pent-3-enyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 62.9 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

2: 82.9 percent / N-methylmorpholine N-oxide; osmium tetraoxide / acetone; H₂O / 4 h / 20 °C

3: 84 percent / pyridine / 2 h / 0 °C

4: 72 percent / pyridinium chlorochromate; 4A MS / CH₂Cl₂ / 4 h / 20 °C

5: 28.9 percent / tetrahydrofuran / 2 h / 50 °C

6: 97.3 percent / tetrabutylammonium fluoride; HOAc / tetrahydrofuran / 2 h / 20 °C

7: 91.1 percent / sodium periodate / ethanol; H₂O / 0.5 h / 20 °C

With pyridine; 1H-imidazole; sodium periodate; osmium(VIII) oxide; tetrabutyl ammonium fluoride; acetic acid; 4-methylmorpholine N-oxide; pyridinium chlorochromate; In tetrahydrofuran; ethanol; dichloromethane; water; acetone;
DOI:10.1021/jo049597h

Reference yield:

: 765311-65-7
(5R)-5,6-di(tert-butyldimethylsilyloxy)-3E-fluoro-1,3-dihexene

: 765311-74-8
Benzoic acid (E)-(S)-2-ethynyl-3-fluoro-2-hydroxy-5-oxo-pent-3-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 82.9 percent / N-methylmorpholine N-oxide; osmium tetraoxide / acetone; H₂O / 4 h / 20 °C

2: 84 percent / pyridine / 2 h / 0 °C

3: 72 percent / pyridinium chlorochromate; 4A MS / CH₂Cl₂ / 4 h / 20 °C

4: 28.9 percent / tetrahydrofuran / 2 h / 50 °C

5: 97.3 percent / tetrabutylammonium fluoride; HOAc / tetrahydrofuran / 2 h / 20 °C

6: 91.1 percent / sodium periodate / ethanol; H₂O / 0.5 h / 20 °C

With pyridine; sodium periodate; osmium(VIII) oxide; tetrabutyl ammonium fluoride; acetic acid; 4-methylmorpholine N-oxide; pyridinium chlorochromate; In tetrahydrofuran; ethanol; dichloromethane; water; acetone;
DOI:10.1021/jo049597h