(-)-[(1R,2R,3S,4S)-2-(benzoyloxy)-4-(benzyloxy)-3-fluoro-5-methylenecyclopentyl]methyl benzoate

Base Information

Chemical Name:(-)-[(1R,2R,3S,4S)-2-(benzoyloxy)-4-(benzyloxy)-3-fluoro-5-methylenecyclopentyl]methyl benzoate
CAS No.:1307273-64-8
Molecular Formula:C₂₈H₂₅FO₅
Molecular Weight:460.502
Hs Code.:

Synonyms:(-)-[(1R,2R,3S,4S)-2-(benzoyloxy)-4-(benzyloxy)-3-fluoro-5-methylenecyclopentyl]methyl benzoate

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Chemical Property of (-)-[(1R,2R,3S,4S)-2-(benzoyloxy)-4-(benzyloxy)-3-fluoro-5-methylenecyclopentyl]methyl benzoate

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Technology Process of (-)-[(1R,2R,3S,4S)-2-(benzoyloxy)-4-(benzyloxy)-3-fluoro-5-methylenecyclopentyl]methyl benzoate

There total 10 articles about (-)-[(1R,2R,3S,4S)-2-(benzoyloxy)-4-(benzyloxy)-3-fluoro-5-methylenecyclopentyl]methyl benzoate 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: 86.0%

: 1338348-10-9
C₁₄H₁₇FO₃

: 98-88-4
benzoyl chloride

: 1307273-64-8
(-)-[(1R,2R,3S,4S)-2-(benzoyloxy)-4-(benzyloxy)-3-fluoro-5-methylenecyclopentyl]methyl benzoate

Guidance literature:: With pyridine; at 20 ℃; for 4h;
DOI:10.1016/j.bmcl.2011.08.113

Reference yield:

: 1307273-60-4
(-)-(1R,2R,3S,5R)-3-(benzyloxy)-5-(hydroxymethyl)-4-methylenecyclopentane-1,2-diol

: 1307273-64-8
(-)-[(1R,2R,3S,4S)-2-(benzoyloxy)-4-(benzyloxy)-3-fluoro-5-methylenecyclopentyl]methyl benzoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridine / -30 - 20 °C

2.1: trifluoromethylsulfonic anhydride; pyridine / dichloromethane / 0.33 h / -78 - 20 °C

2.2: 0.5 h / 50 °C

2.3: 3 h / 20 °C

3.1: diethylamino-sulfur trifluoride / dichloromethane / 0.33 h / 20 °C

4.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 1 h / 20 °C

5.1: pyridine / 4 h / 20 °C

With pyridine; trifluoromethylsulfonic anhydride; diethylamino-sulfur trifluoride; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; dichloromethane;

Reference yield:

: 1307273-58-0
(3aS,4S,6R,6aR)-6-(tert-butoxymethyl)-2,2-dimethyl-5-methylenetetrahydro-3aH-cyclopenta[d][1,3]-dioxol-4-ol

: 1307273-64-8
(-)-[(1R,2R,3S,4S)-2-(benzoyloxy)-4-(benzyloxy)-3-fluoro-5-methylenecyclopentyl]methyl benzoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium hydride / tetrahydrofuran / 0.25 h / 20 °C

1.2: 3.5 h / 40 °C

2.1: hydrogenchloride; water / methanol / 3.5 h / Reflux

3.1: pyridine / -30 - 20 °C

4.1: trifluoromethylsulfonic anhydride; pyridine / dichloromethane / 0.33 h / -78 - 20 °C

4.2: 0.5 h / 50 °C

4.3: 3 h / 20 °C

5.1: diethylamino-sulfur trifluoride / dichloromethane / 0.33 h / 20 °C

6.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 1 h / 20 °C

7.1: pyridine / 4 h / 20 °C

With pyridine; hydrogenchloride; trifluoromethylsulfonic anhydride; diethylamino-sulfur trifluoride; tetrabutyl ammonium fluoride; water; sodium hydride; acetic acid; In tetrahydrofuran; methanol; dichloromethane;