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

Base Information

• Chemical Name: 3α,5α-dihydroxy-2β-(benzyloxymethyl)cyclopentane-1α-acetic acid γ-lactone 3-tetrahydropyran-2-yl ether
• CAS No.: 32233-38-8
• Molecular Formula: C₂₀H₂₆O₅
• Molecular Weight: 346.423
• Mol file: 32233-38-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 5 articles about 3α,5α-dihydroxy-2β-(benzyloxymethyl)cyclopentane-1α-acetic acid γ-lactone 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:

(3aR,4S,5S,6R,6aR)-4-Benzyloxymethyl-6-iodo-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one (62447-84-1) → 3α,5α-dihydroxy-2β-(benzyloxymethyl)cyclopentane-1α-acetic acid γ-lactone 3-tetrahydropyran-2-yl ether (32233-38-8)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene;

DOI:10.1016/0040-4039(91)80038-8

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → 3α,5α-dihydroxy-2β-(benzyloxymethyl)cyclopentane-1α-acetic acid γ-lactone 3-tetrahydropyran-2-yl ether (32233-38-8)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH / CH₂Cl₂

2: Bu₃SnH, AIBN / benzene

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; toluene-4-sulfonic acid; In dichloromethane; benzene;

DOI:10.1016/0040-4039(91)80038-8

Reference yield:

6-Benzyloxymethyl-7-hydroxy-8-iodo-2-oxabicyclo<3.3.0>octan-3-one (31767-37-0) → 3α,5α-dihydroxy-2β-(benzyloxymethyl)cyclopentane-1α-acetic acid γ-lactone 3-tetrahydropyran-2-yl ether (32233-38-8)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH / CH₂Cl₂

2: Bu₃SnH, AIBN / benzene

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; toluene-4-sulfonic acid; In dichloromethane; benzene;

DOI:10.1016/0040-4039(91)80038-8

upstream raw materials:

(3aR,4S,5S,6R,6aR)-4-Benzyloxymethyl-6-iodo-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one

3,4-dihydro-2H-pyran

6-Benzyloxymethyl-7-hydroxy-8-iodo-2-oxabicyclo<3.3.0>octan-3-one

Downstream raw materials:

(3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one

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