(3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((3R)-3-hydroxy-4-phenoxy-1(E)-butenyl)-2H-cyclopentafuran-2-one

Base Information

• Chemical Name: (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((3R)-3-hydroxy-4-phenoxy-1(E)-butenyl)-2H-cyclopentafuran-2-one
• CAS No.: 51638-92-7
• Molecular Formula: C₂₄H₂₄O₆
• Molecular Weight: 408.451

Synonyms:(3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((3R)-3-hydroxy-4-phenoxy-1(E)-butenyl)-2H-cyclopentafuran-2-one

Chemical Property of (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((3R)-3-hydroxy-4-phenoxy-1(E)-butenyl)-2H-cyclopentafuran-2-one

Chemical Property:

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Technology Process of (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((3R)-3-hydroxy-4-phenoxy-1(E)-butenyl)-2H-cyclopentafuran-2-one

There total 11 articles about (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((3R)-3-hydroxy-4-phenoxy-1(E)-butenyl)-2H-cyclopentafuran-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: 80.0%

(3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((2R)-2-(phenylsulfinyl)-(3S)-3-hydroxy-4-phenoxybutyl)-2H-cyclopentafuran-2-one (131543-67-4,131615-45-7) → (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((3R)-3-hydroxy-4-phenoxy-1(E)-butenyl)-2H-cyclopentafuran-2-one (51638-92-7)

Guidance literature:

With calcium carbonate; In toluene; for 24h; Heating;

DOI:10.1021/jo00003a083

Reference yield: 50.0%

(3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate (51638-91-6) → (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((3R)-3-hydroxy-4-phenoxy-1(E)-butenyl)-2H-cyclopentafuran-2-one (51638-92-7)

Guidance literature:

With (-)-diisopinocamphenylborane chloride; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/j.bmc.2004.04.034

Reference yield: 35.0%

(3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate (51638-91-6) → (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((3R)-3-hydroxy-4-phenoxy-1(E)-butenyl)-2H-cyclopentafuran-2-one (51638-92-7) + [3aR,4R(1E,3S),5R,6aS]-5-benzoyloxy-4-(3-hydroxy-4-phenoxy-1-buten-1-yl)-hexahydro-2H-cyclopenta[b]furan-2-one (51705-18-1)

Guidance literature:

With (+)-β-chlorodiisopinocampheylborane; In tetrahydrofuran; at 0 ℃; for 1.5h;

DOI:10.1016/j.bmc.2004.04.034

upstream raw materials:

(3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((2R)-2-(phenylsulfinyl)-(3S)-3-hydroxy-4-phenoxybutyl)-2H-cyclopentafuran-2-one

(3aR,4R,5R,6aS)-2-oxo-4-((E)-3-oxo-4-phenoxybut-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-5-yl benzoate

(1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one

(3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-(bromomethyl)-2H-cyclopentafuran-2-one

Downstream raw materials:

[3aR,4R(3R),5R,6aS]-5-benzoyloxy-4-(3-hydroxy-4-phenoxybutyl)-hexahydro-2H-cyclopenta[b]furan-2-one

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