6(S)-{2(E)-[4-bromo-2(S)-hydroxy-2-(1(R)-hydroxy-5-phenyl-pentyl)-5-oxo-cyclopent-3-enylidene]-1(R)-hydroxy-ethyl}-tetrahydropyran-2-one

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Chemical Name:6(S)-{2(E)-[4-bromo-2(S)-hydroxy-2-(1(R)-hydroxy-5-phenyl-pentyl)-5-oxo-cyclopent-3-enylidene]-1(R)-hydroxy-ethyl}-tetrahydropyran-2-one
CAS No.:753497-81-3
Molecular Formula:C₂₃H₂₇BrO₆
Molecular Weight:479.368
Hs Code.:

Synonyms:6(S)-{2(E)-[4-bromo-2(S)-hydroxy-2-(1(R)-hydroxy-5-phenyl-pentyl)-5-oxo-cyclopent-3-enylidene]-1(R)-hydroxy-ethyl}-tetrahydropyran-2-one

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Chemical Property of 6(S)-{2(E)-[4-bromo-2(S)-hydroxy-2-(1(R)-hydroxy-5-phenyl-pentyl)-5-oxo-cyclopent-3-enylidene]-1(R)-hydroxy-ethyl}-tetrahydropyran-2-one

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Technology Process of 6(S)-{2(E)-[4-bromo-2(S)-hydroxy-2-(1(R)-hydroxy-5-phenyl-pentyl)-5-oxo-cyclopent-3-enylidene]-1(R)-hydroxy-ethyl}-tetrahydropyran-2-one

There total 5 articles about 6(S)-{2(E)-[4-bromo-2(S)-hydroxy-2-(1(R)-hydroxy-5-phenyl-pentyl)-5-oxo-cyclopent-3-enylidene]-1(R)-hydroxy-ethyl}-tetrahydropyran-2-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: 58.0%

: 753497-77-7
(4R)-{5(S)-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenylbutyl)-1,3-dioxa-spiro[4.4]non-8-en-6(E)-ylidenemethyl]-(2,2-dimethyl-[1,3]dioxolan-(3R)-(4S)-yl)}-butyric acid methyl ester

: 753497-81-3
6(S)-{2(E)-[4-bromo-2(S)-hydroxy-2-(1(R)-hydroxy-5-phenyl-pentyl)-5-oxo-cyclopent-3-enylidene]-1(R)-hydroxy-ethyl}-tetrahydropyran-2-one

: 6(E)-[8-bromo-2(S)-hydroxy-2-(1(R)-hydroxy-5(S)-phenylpentyl)-5-oxo-cyclopent-3-enylidene]-(5R),(6R)-dihydroxy-heptanoic acid methyl ester

Guidance literature:: With trifluoroacetic acid; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1039/b404016c

Reference yield:

: 102354-82-5
methyl 4-(5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl)butanoate

: 753497-81-3
6(S)-{2(E)-[4-bromo-2(S)-hydroxy-2-(1(R)-hydroxy-5-phenyl-pentyl)-5-oxo-cyclopent-3-enylidene]-1(R)-hydroxy-ethyl}-tetrahydropyran-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: LDA / tetrahydrofuran / 0.25 h / -78 °C

1.2: 41.6 percent / tetrahydrofuran / 0.5 h / -78 °C

2.1: 61 percent / Ac₂O; 4-DMAP; pyridine / 4 h / 60 °C

3.1: 58 percent / aq. TFA / tetrahydrofuran / 1 h / 20 °C

With pyridine; dmap; acetic anhydride; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran;
DOI:10.1039/b404016c

Reference yield:

: 2,2-dimethyl-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]non-8-en-7-one

: 753497-81-3
6(S)-{2(E)-[4-bromo-2(S)-hydroxy-2-(1(R)-hydroxy-5-phenyl-pentyl)-5-oxo-cyclopent-3-enylidene]-1(R)-hydroxy-ethyl}-tetrahydropyran-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 300 mg / Br₂ / CH₂Cl₂ / 0.4 h

2.1: LDA / tetrahydrofuran / 0.25 h / -78 °C

2.2: 41.6 percent / tetrahydrofuran / 0.5 h / -78 °C

3.1: 61 percent / Ac₂O; 4-DMAP; pyridine / 4 h / 60 °C

4.1: 58 percent / aq. TFA / tetrahydrofuran / 1 h / 20 °C

With pyridine; dmap; bromine; acetic anhydride; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;
DOI:10.1039/b404016c