3α-hydroxy-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane tetrahydropyranyl ether (β-isomer)

Base Information

• Chemical Name: 3α-hydroxy-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane tetrahydropyranyl ether (β-isomer)
• CAS No.: 74028-42-5
• Molecular Formula: C₂₁H₂₈O₄
• Molecular Weight: 344.451
• Mol file: 74028-42-5.mol

Synonyms:3α-hydroxy-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane tetrahydropyranyl ether (β-isomer)

Chemical Property of 3α-hydroxy-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane tetrahydropyranyl ether (β-isomer)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3α-hydroxy-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane tetrahydropyranyl ether (β-isomer)

There total 15 articles about 3α-hydroxy-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane tetrahydropyranyl ether (β-isomer) 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: 54.0%

methyl 3α-hydroxy-2β-(benzyloxymethyl)-5ξ-(carbomethoxymethyl)cyclopentane-1ξ-acetate tetrahydropyran-2-yl ether (73995-84-3,120926-22-9) → 3α-hydroxy-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane tetrahydropyranyl ether (β-isomer) (74028-42-5) + 3α-hydroxy-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane tetrahydropyranyl ether (α-isomer) (73996-31-3)

Guidance literature:

With potassium tert-butylate; Yield given. Multistep reaction; 1.) benzene, 30 deg C (adding), then 70 deg C, 4 h, 2.) HMPA-H₂O, 175 deg C, 15 min;

DOI:10.1016/0040-4020(81)80005-1

Reference yield:

3α,5α-dihydroxy-2β-(benzyloxymethyl)cyclopentane-1α-acetic acid γ-lactone 3-tetrahydropyran-2-yl ether (32233-38-8) → 3α-hydroxy-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane tetrahydropyranyl ether (β-isomer) (74028-42-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 2 N NaOH / methanol / 0.5 h / Ambient temperature

2: diethyl ether / 5 °C

3: 1.) chromyl chloride / 1.) CH₂Cl₂, t-BuOH, pyridine, CCl₄, -78 deg C, 40 min (prep. of reagent), 2.) CH₂Cl₂, up to RT, then 35 deg C, 2.5 h

4: 46 percent / 1.) diisopropylamine, n-butyllithium / 1.) THF, hexane, -78 deg C, 15 min, 2.) -78 deg, 20 min, 3.) THF, -78 deg C, 10 min (adding), then same temp, 2 h

5: 91 percent / H₂ / 5percent Pd-C / ethanol / 1.6 h / Ambient temperature

6: 37 percent / 1.) potassium t-butoxide / 1.) benzene, 30 deg C (adding), then 70 deg C, 4 h, 2.) HMPA-H₂O, 175 deg C, 15 min

With sodium hydroxide; n-butyllithium; potassium tert-butylate; hydrogen; chromyl chloride; diisopropylamine; palladium on activated charcoal; In methanol; diethyl ether; ethanol;

DOI:10.1016/0040-4020(81)80005-1

Reference yield:

[(1R,2S,3R)-2-Benzyloxymethyl-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester (74028-40-3) → 3α-hydroxy-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane tetrahydropyranyl ether (β-isomer) (74028-42-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) chromyl chloride / 1.) CH₂Cl₂, t-BuOH, pyridine, CCl₄, -78 deg C, 40 min (prep. of reagent), 2.) CH₂Cl₂, up to RT, then 35 deg C, 2.5 h

2: 46 percent / 1.) diisopropylamine, n-butyllithium / 1.) THF, hexane, -78 deg C, 15 min, 2.) -78 deg, 20 min, 3.) THF, -78 deg C, 10 min (adding), then same temp, 2 h

3: 91 percent / H₂ / 5percent Pd-C / ethanol / 1.6 h / Ambient temperature

4: 37 percent / 1.) potassium t-butoxide / 1.) benzene, 30 deg C (adding), then 70 deg C, 4 h, 2.) HMPA-H₂O, 175 deg C, 15 min

With n-butyllithium; potassium tert-butylate; hydrogen; chromyl chloride; diisopropylamine; palladium on activated charcoal; In ethanol;

DOI:10.1016/0040-4020(81)80005-1

upstream raw materials:

methyl 3α-hydroxy-2β-(benzyloxymethyl)-5ξ-(carbomethoxymethyl)cyclopentane-1ξ-acetate tetrahydropyran-2-yl ether

3α,5α-dihydroxy-2β-(benzyloxymethyl)cyclopentane-1α-acetic acid γ-lactone 3-tetrahydropyran-2-yl ether

methyl 3α-hydroxy-5-oxo-2β-(benzyloxymethyl)cyclopentane-1α-acetate 3-tetrahydropyran-2-yl ether

methyl 3α-hydroxy-2β-(benzyloxymethyl)-5-(carbomethoxymethylene)cyclopentane-1α-acetate 3-tetrahydropyran-2-yl ether

Downstream raw materials:

3α-hydroxy-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane (β-isomer)