((1R,5S)-5-Benzyloxy-cyclopent-2-enyl)-fluoro-acetic acid tert-butyl ester

Base Information

Chemical Name:((1R,5S)-5-Benzyloxy-cyclopent-2-enyl)-fluoro-acetic acid tert-butyl ester
CAS No.:783345-25-5
Molecular Formula:C₁₈H₂₃FO₃
Molecular Weight:306.377
Hs Code.:

Synonyms:((1R,5S)-5-Benzyloxy-cyclopent-2-enyl)-fluoro-acetic acid tert-butyl ester

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Chemical Property of ((1R,5S)-5-Benzyloxy-cyclopent-2-enyl)-fluoro-acetic acid tert-butyl ester

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Technology Process of ((1R,5S)-5-Benzyloxy-cyclopent-2-enyl)-fluoro-acetic acid tert-butyl ester

There total 6 articles about ((1R,5S)-5-Benzyloxy-cyclopent-2-enyl)-fluoro-acetic acid tert-butyl 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: 80.0%

: 783345-23-3
((1R,5S)-5-Benzyloxy-cyclopent-2-enyl)-acetic acid tert-butyl ester

: 783345-25-5
((1R,5S)-5-Benzyloxy-cyclopent-2-enyl)-fluoro-acetic acid tert-butyl ester

Guidance literature:: With N-fluorobis(benzenesulfon)imide; lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/j.tetlet.2004.08.027

Reference yield:

: 60410-16-4
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate

: 783345-25-5
((1R,5S)-5-Benzyloxy-cyclopent-2-enyl)-fluoro-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 48 percent / NaH / dimethylformamide / 0 - 20 °C

2: LDA; HMPA / tetrahydrofuran / -78 - 20 °C

3: xylene / 130 °C

4: aq. NaOH / tetrahydrofuran / 20 °C

5: 53 percent / DCC; DMAP / CH₂Cl₂ / 0 - 20 °C

6: 80 percent / LDA; (PhSO₂)2NF / tetrahydrofuran / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; sodium hydride; N-fluorobis(benzenesulfon)imide; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; xylene; 3: Ireland-Claisen rearrangement;
DOI:10.1016/j.tetlet.2004.08.027

Reference yield:

: 100-39-0
benzyl bromide

: 783345-25-5
((1R,5S)-5-Benzyloxy-cyclopent-2-enyl)-fluoro-acetic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 48 percent / NaH / dimethylformamide / 0 - 20 °C

2: LDA; HMPA / tetrahydrofuran / -78 - 20 °C

3: xylene / 130 °C

4: aq. NaOH / tetrahydrofuran / 20 °C

5: 53 percent / DCC; DMAP / CH₂Cl₂ / 0 - 20 °C

6: 80 percent / LDA; (PhSO₂)2NF / tetrahydrofuran / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; sodium hydride; N-fluorobis(benzenesulfon)imide; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; xylene; 3: Ireland-Claisen rearrangement;
DOI:10.1016/j.tetlet.2004.08.027