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

Base Information

• Chemical Name: methyl 3α-hydroxy-2β-(benzyloxymethyl)-5ξ-(carbomethoxymethyl)cyclopentane-1ξ-acetate tetrahydropyran-2-yl ether
• CAS No.: 73995-84-3
• Molecular Formula: C₂₄H₃₄O₇
• Molecular Weight: 434.53
• Mol file: 73995-84-3.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about methyl 3α-hydroxy-2β-(benzyloxymethyl)-5ξ-(carbomethoxymethyl)cyclopentane-1ξ-acetate tetrahydropyran-2-yl ether 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: 91.0%

methyl 3α-hydroxy-2β-(benzyloxymethyl)-5-(carbomethoxymethylene)cyclopentane-1α-acetate 3-tetrahydropyran-2-yl ether (74080-58-3) → methyl 3α-hydroxy-2β-(benzyloxymethyl)-5ξ-(carbomethoxymethyl)cyclopentane-1ξ-acetate tetrahydropyran-2-yl ether (73995-84-3,120926-22-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 1.6h; Ambient temperature;

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) → methyl 3α-hydroxy-2β-(benzyloxymethyl)-5ξ-(carbomethoxymethyl)cyclopentane-1ξ-acetate tetrahydropyran-2-yl ether (73995-84-3,120926-22-9)

Guidance literature:

Multi-step reaction with 5 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

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

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

Reference yield:

methyl 3α-hydroxy-5-oxo-2β-(benzyloxymethyl)cyclopentane-1α-acetate 3-tetrahydropyran-2-yl ether (74163-85-2) → methyl 3α-hydroxy-2β-(benzyloxymethyl)-5ξ-(carbomethoxymethyl)cyclopentane-1ξ-acetate tetrahydropyran-2-yl ether (73995-84-3,120926-22-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 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

2: 91 percent / H₂ / 5percent Pd-C / ethanol / 1.6 h / Ambient temperature

With n-butyllithium; hydrogen; diisopropylamine; palladium on activated charcoal; In ethanol;

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

upstream raw materials:

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

[(1R,2S,3R)-2-Benzyloxymethyl-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid

Downstream raw materials:

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

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

(5E)-6a-carbaprostaglandin I₂ methyl ester

(5E,16R)-6α-carbaprostaglandin I₂ methyl ester