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

Base Information

• Chemical Name: (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-(iodomethyl)-2H-cyclopentafuran-2-one
• CAS No.: 131543-60-7
• Molecular Formula: C₁₅H₁₅IO₄
• Molecular Weight: 386.186

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

Chemical Property of (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-(iodomethyl)-2H-cyclopentafuran-2-one

Chemical Property:

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Technology Process of (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-(iodomethyl)-2H-cyclopentafuran-2-one

There total 2 articles about (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-(iodomethyl)-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: 93.0%

(1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one (39746-00-4,172821-93-1) → (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-(iodomethyl)-2H-cyclopentafuran-2-one (131543-60-7)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1039/c8ob00489g

Reference yield: 80.0%

(3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-(bromomethyl)-2H-cyclopentafuran-2-one (131543-59-4) → (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-(iodomethyl)-2H-cyclopentafuran-2-one (131543-60-7)

Guidance literature:

With sodium iodide; In acetone; for 1h; Heating;

DOI:10.1021/jo00003a083

Reference yield: 97.0%

(3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-(iodomethyl)-2H-cyclopentafuran-2-one (131543-60-7) → (3aR,5R,6aS)-4-methylene-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 60 ℃; for 16h; Inert atmosphere;

DOI:10.1039/c8ob00489g

upstream raw materials:

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

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

Downstream raw materials:

(3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-(4-(tert-butyldimethylsiloxy)-2(E)-butenyl)-2H-cyclopentafuran-2-one

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

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

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

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