[3aR,4R(1E,3S),5R,6aS]-4-[3-cyclohexyl-3-hydroxy-1-propenyl]-5-(benzoyloxy)hexahydro-2H-cyclopenta[b]furan-2-one

Base Information

• Chemical Name: [3aR,4R(1E,3S),5R,6aS]-4-[3-cyclohexyl-3-hydroxy-1-propenyl]-5-(benzoyloxy)hexahydro-2H-cyclopenta[b]furan-2-one
• CAS No.: 170290-68-3
• Molecular Formula: C₂₃H₂₈O₅
• Molecular Weight: 384.472

Synonyms:[3aR,4R(1E,3S),5R,6aS]-4-[3-cyclohexyl-3-hydroxy-1-propenyl]-5-(benzoyloxy)hexahydro-2H-cyclopenta[b]furan-2-one

Chemical Property of [3aR,4R(1E,3S),5R,6aS]-4-[3-cyclohexyl-3-hydroxy-1-propenyl]-5-(benzoyloxy)hexahydro-2H-cyclopenta[b]furan-2-one

Chemical Property:

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Technology Process of [3aR,4R(1E,3S),5R,6aS]-4-[3-cyclohexyl-3-hydroxy-1-propenyl]-5-(benzoyloxy)hexahydro-2H-cyclopenta[b]furan-2-one

There total 3 articles about [3aR,4R(1E,3S),5R,6aS]-4-[3-cyclohexyl-3-hydroxy-1-propenyl]-5-(benzoyloxy)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:

dimethyl (2-cyclohexyl-2-oxoethyl)phosphonate (58009-66-8) → [3aR,4R(1E,3S),5R,6aS]-4-[3-cyclohexyl-3-hydroxy-1-propenyl]-5-(benzoyloxy)hexahydro-2H-cyclopenta[b]furan-2-one (170290-68-3)

Guidance literature:

Multi-step reaction with 2 steps

1: LiCl; Et₃N / tetrahydrofuran; CH₂Cl₂

2: NaBH₄; CeCl₃*7H₂O / methanol

With sodium tetrahydroborate; cerium(III) chloride; triethylamine; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; 1: Condensation / 2: Reduction;

DOI:10.1016/S0040-4039(00)00973-4

Reference yield:

(1S,5R,6R,7R)-6-formyl-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one (39746-01-5) → [3aR,4R(1E,3S),5R,6aS]-4-[3-cyclohexyl-3-hydroxy-1-propenyl]-5-(benzoyloxy)hexahydro-2H-cyclopenta[b]furan-2-one (170290-68-3)

Guidance literature:

Multi-step reaction with 2 steps

1: LiCl; Et₃N / tetrahydrofuran; CH₂Cl₂

2: NaBH₄; CeCl₃*7H₂O / methanol

With sodium tetrahydroborate; cerium(III) chloride; triethylamine; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; 1: Condensation / 2: Reduction;

DOI:10.1016/S0040-4039(00)00973-4

Reference yield:

(3aR,4R,5R,6aS)-5-(Benzoyloxy)4-[(E)-3-cyclohexyl-3-oxo-1-propenyl]-hexahydro-2H-cyclopenta[b]furan-2-one (170290-67-2) → Benzoic acid (3aR,4R,5R,6aS)-4-((E)-(R)-3-cyclohexyl-3-hydroxy-propenyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester + [3aR,4R(1E,3S),5R,6aS]-4-[3-cyclohexyl-3-hydroxy-1-propenyl]-5-(benzoyloxy)hexahydro-2H-cyclopenta[b]furan-2-one (170290-68-3)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol;

DOI:10.1016/S0040-4039(00)00973-4

upstream raw materials:

(3aR,4R,5R,6aS)-5-(Benzoyloxy)4-[(E)-3-cyclohexyl-3-oxo-1-propenyl]-hexahydro-2H-cyclopenta[b]furan-2-one

dimethyl (2-cyclohexyl-2-oxoethyl)phosphonate

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

Downstream raw materials:

(1S,2R,3R,4R)-3-[(R)-3-Cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-4-(tetrahydro-pyran-2-yloxy)-2-[(Z)-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-hex-2-enyl]-cyclopentanol

C₃₆H₆₂BClO₆

(3aR,4R,5R,6aS)-4-[(R)-3-Cyclohexyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol

[3aR,4R(1E,3S),5R,6aS]-4-[3-cyclohexyl-3-(tetrahydropyran-2-yloxy)propyl]-5-(tetrahydropyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one

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