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

Base Information

• Chemical Name: methyl 3α-hydroxy-2β-(benzyloxymethyl)-5-(carbomethoxymethylene)cyclopentane-1α-acetate 3-tetrahydropyran-2-yl ether
• CAS No.: 74080-58-3
• Molecular Formula: C₂₄H₃₂O₇
• Molecular Weight: 432.514
• Mol file: 74080-58-3.mol

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

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

There total 12 articles about methyl 3α-hydroxy-2β-(benzyloxymethyl)-5-(carbomethoxymethylene)cyclopentane-1α-acetate 3-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: 76.0%

methanol (67-56-1) + [(4S,5R)-4-Benzyloxymethyl-2-oxo-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-6a-yl]-trimethylsilanyl-acetic acid methyl ester (82259-28-7) → methyl 3α-hydroxy-2β-(benzyloxymethyl)-5-(carbomethoxymethylene)cyclopentane-1α-acetate 3-tetrahydropyran-2-yl ether (74080-58-3)

Guidance literature:

With potassium fluoride; at 20 ℃; for 0.5h;

Reference yield: 46.0%

methyl (trimethylsilyl)acetate (2916-76-9) + methyl 3α-hydroxy-5-oxo-2β-(benzyloxymethyl)cyclopentane-1α-acetate 3-tetrahydropyran-2-yl ether (74163-85-2) → methyl 3α-hydroxy-2β-(benzyloxymethyl)-5-(carbomethoxymethylene)cyclopentane-1α-acetate 3-tetrahydropyran-2-yl ether (74080-58-3) + [(4S,5R)-4-Benzyloxymethyl-2-oxo-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-6a-yl]-trimethylsilanyl-acetic acid methyl ester (82259-28-7)

Guidance literature:

With n-butyllithium; diisopropylamine; Yield given. Multistep reaction; 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;

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)-5-(carbomethoxymethylene)cyclopentane-1α-acetate 3-tetrahydropyran-2-yl ether (74080-58-3)

Guidance literature:

Multi-step reaction with 4 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

With sodium hydroxide; n-butyllithium; chromyl chloride; diisopropylamine; In methanol; diethyl ether;

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

upstream raw materials:

diazomethane

[(4S,5R)-4-Benzyloxymethyl-2-oxo-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-6a-yl]-trimethylsilanyl-acetic acid methyl ester

methyl (trimethylsilyl)acetate

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

Downstream raw materials:

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

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)

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