(3aR,4R,5R,6aS)-5-((t-butyldimethylsilyl)oxy)-4-((3R,4R,E)-3-((t-butyldimethylsilyl)oxy)-4-(m-tolyl)pent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one

Base Information

Chemical Name:(3aR,4R,5R,6aS)-5-((t-butyldimethylsilyl)oxy)-4-((3R,4R,E)-3-((t-butyldimethylsilyl)oxy)-4-(m-tolyl)pent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one
CAS No.:1215192-65-6
Molecular Formula:C₃₁H₅₂O₄Si₂
Molecular Weight:544.922
Hs Code.:

Synonyms:(3aR,4R,5R,6aS)-5-((t-butyldimethylsilyl)oxy)-4-((3R,4R,E)-3-((t-butyldimethylsilyl)oxy)-4-(m-tolyl)pent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one

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Chemical Property of (3aR,4R,5R,6aS)-5-((t-butyldimethylsilyl)oxy)-4-((3R,4R,E)-3-((t-butyldimethylsilyl)oxy)-4-(m-tolyl)pent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one

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Technology Process of (3aR,4R,5R,6aS)-5-((t-butyldimethylsilyl)oxy)-4-((3R,4R,E)-3-((t-butyldimethylsilyl)oxy)-4-(m-tolyl)pent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one

There total 7 articles about (3aR,4R,5R,6aS)-5-((t-butyldimethylsilyl)oxy)-4-((3R,4R,E)-3-((t-butyldimethylsilyl)oxy)-4-(m-tolyl)pent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-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:

: 1215192-64-5
(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3R,4R)-3-hydroxy-4-(m-tolyl)pent-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1215192-65-6
(3aR,4R,5R,6aS)-5-((t-butyldimethylsilyl)oxy)-4-((3R,4R,E)-3-((t-butyldimethylsilyl)oxy)-4-(m-tolyl)pent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 2.5h;

Reference yield:

: 1215192-62-3
(1S,5R,6R,7R)-6-[(1E,4R)-3-oxo-4-(m-tolyl)-1-pentenyl]-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one

: 1215192-65-6
(3aR,4R,5R,6aS)-5-((t-butyldimethylsilyl)oxy)-4-((3R,4R,E)-3-((t-butyldimethylsilyl)oxy)-4-(m-tolyl)pent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: (-)-diisopinocampheyl chloride / hexane; tetrahydrofuran; acetone / -40 °C / Cooling with ice

2.1: potassium carbonate / methanol / 17 h / 20 °C

2.2: pH 7

3.1: 1H-imidazole / N,N-dimethyl-formamide / 2.5 h

With 1H-imidazole; (-)-diisopinocampheyl chloride; potassium carbonate; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide; acetone;

Reference yield:

: (R)-2-(3-methylphenyl)propionic acid methyl ester

: 1215192-65-6
(3aR,4R,5R,6aS)-5-((t-butyldimethylsilyl)oxy)-4-((3R,4R,E)-3-((t-butyldimethylsilyl)oxy)-4-(m-tolyl)pent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 2 h / -78 °C

2.1: sodium hydride / 1,2-dimethoxyethane / 1 h

2.2: 1 h

3.1: (-)-diisopinocampheyl chloride / hexane; tetrahydrofuran; acetone / -40 °C / Cooling with ice

4.1: potassium carbonate / methanol / 17 h / 20 °C

4.2: pH 7

5.1: 1H-imidazole / N,N-dimethyl-formamide / 2.5 h

With 1H-imidazole; n-butyllithium; (-)-diisopinocampheyl chloride; sodium hydride; potassium carbonate; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; N,N-dimethyl-formamide; acetone;