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

Base Information

• Chemical Name: (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((2R,3R)-2,3-epoxy-4-hydroxybutyl)-2H-cyclopentafuran-2-one
• CAS No.: 131543-64-1
• Molecular Formula: C₁₈H₂₀O₆
• Molecular Weight: 332.353

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

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

Chemical Property:

Purity/Quality:

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

There total 10 articles about (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((2R,3R)-2,3-epoxy-4-hydroxybutyl)-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: 92.0%

(3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-(4-hydroxy-2(E)-butenyl)-2H-cyclopentafuran-2-one (131543-63-0) → (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-((2R,3R)-2,3-epoxy-4-hydroxybutyl)-2H-cyclopentafuran-2-one (131543-64-1)

Guidance literature:

With titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; In dichloromethane; at -20 ℃; for 11h;

DOI:10.1021/jo00003a083

Reference yield:

(1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one (39746-00-4,172821-93-1) → Benzoic acid (3aR,4R,5R,6aS)-4-(3-hydroxymethyl-oxiranylmethyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (131543-64-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / CBr₄, Ph₃P / acetonitrile / 1 h / Ambient temperature

2: 80 percent / NaI / acetone / 1 h / Heating

4: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

5: m-chloroperbenzoic acid

With carbon tetrabromide; tetrabutyl ammonium fluoride; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; sodium iodide; In tetrahydrofuran; acetone; acetonitrile;

DOI:10.1021/jo00003a083

Reference yield:

(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-((2R,3R)-2,3-epoxy-4-hydroxybutyl)-2H-cyclopentafuran-2-one (131543-64-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / CBr₄, Ph₃P / acetonitrile / 1 h / Ambient temperature

2: 80 percent / NaI / acetone / 1 h / Heating

4: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

5: 92 percent / titanium tetraisopropoxide, L-(+)-diethyl tartrate / CH₂Cl₂ / 11 h / -20 °C

With titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; carbon tetrabromide; tetrabutyl ammonium fluoride; triphenylphosphine; sodium iodide; In tetrahydrofuran; dichloromethane; acetone; acetonitrile;

DOI:10.1021/jo00003a083

upstream raw materials:

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

(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

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

Downstream raw materials:

(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-((2R)-2-(phenylsulfinyl)-(3S)-3-hydroxy-4-phenoxybutyl)-2H-cyclopentafuran-2-one

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

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

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