(3aR,4R,5R,6aS)-5-(tert-butyldiphenylsilyloxy)-4-((S,E)-3-hydroxy-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-one

Base Information

Chemical Name:(3aR,4R,5R,6aS)-5-(tert-butyldiphenylsilyloxy)-4-((S,E)-3-hydroxy-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-one
CAS No.:1395619-12-1
Molecular Formula:C₃₄H₄₀O₄Si
Molecular Weight:540.775
Hs Code.:

Synonyms:(3aR,4R,5R,6aS)-5-(tert-butyldiphenylsilyloxy)-4-((S,E)-3-hydroxy-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-one

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Chemical Property of (3aR,4R,5R,6aS)-5-(tert-butyldiphenylsilyloxy)-4-((S,E)-3-hydroxy-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-one

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Technology Process of (3aR,4R,5R,6aS)-5-(tert-butyldiphenylsilyloxy)-4-((S,E)-3-hydroxy-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-one

There total 8 articles about (3aR,4R,5R,6aS)-5-(tert-butyldiphenylsilyloxy)-4-((S,E)-3-hydroxy-5-phenylpent-1-enyl)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: 70.0%

: 1395619-06-3
(3aR,4R,5R,6aS)-5-(tert-butyldiphenylsilyloxy)-4-((E)-3-oxo-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-one

: 1395619-12-1
(3aR,4R,5R,6aS)-5-(tert-butyldiphenylsilyloxy)-4-((S,E)-3-hydroxy-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-one

Guidance literature:: With (-)-diisopinocamphenylborane chloride; In tetrahydrofuran; at 0 ℃; for 2h; Inert atmosphere;

Reference yield:

: 32233-40-2
(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

: 1395619-12-1
(3aR,4R,5R,6aS)-5-(tert-butyldiphenylsilyloxy)-4-((S,E)-3-hydroxy-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: dmap; triethylamine / dichloromethane / 4 h / 20 °C / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / Inert atmosphere

3.1: sulfuric acid / methanol / 4 h / 20 °C / Inert atmosphere

4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 4 h

5.1: triethylamine; lithium chloride / tetrahydrofuran / 1.5 h / -10 °C / Inert atmosphere

5.2: 2.42 h / -10 °C / Inert atmosphere

6.1: (-)-diisopinocamphenylborane chloride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

With 1H-imidazole; dmap; sulfuric acid; triethylamine; (-)-diisopinocamphenylborane chloride; lithium chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 5.1: Horner-Wadsworth-Emmons Olefination;

Reference yield:

: (3aR,4S,5R,6aS)-5-{[(tert-butyl)(diphenyl)silyl]oxy}-3,3a,4,5,6,6a-hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one

: 1395619-12-1
(3aR,4R,5R,6aS)-5-(tert-butyldiphenylsilyloxy)-4-((S,E)-3-hydroxy-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 4 h

2.1: triethylamine; lithium chloride / tetrahydrofuran / 1.5 h / -10 °C / Inert atmosphere

2.2: 2.42 h / -10 °C / Inert atmosphere

3.1: (-)-diisopinocamphenylborane chloride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

With triethylamine; (-)-diisopinocamphenylborane chloride; lithium chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dimethyl sulfoxide; 2.1: Horner-Wadsworth-Emmons Olefination;