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

Base Information

• Chemical Name: [(4S,5R)-4-Benzyloxymethyl-2-oxo-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-6a-yl]-trimethylsilanyl-acetic acid methyl ester
• CAS No.: 82259-28-7
• Molecular Formula: C₂₆H₃₈O₇Si
• Molecular Weight: 490.669
• Mol file: 82259-28-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

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: 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

Reference yield:

[(1R,2S,3R)-2-Benzyloxymethyl-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid (74028-39-0,87302-49-6) → [(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:

Multi-step reaction with 3 steps

1: diethyl ether / 5 °C

2: 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

3: 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 n-butyllithium; chromyl chloride; diisopropylamine; In diethyl ether;

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

upstream raw materials:

methyl (trimethylsilyl)acetate

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

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

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

Downstream raw materials:

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

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

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)