6-{(1E)(3S)-3-(2H-3,4,5,6-tetrahydropyran-2-yloxy)-4-[3-(methoxymethyl)phenyl]but-1-enyl}-7-(2H-3,4,5,6-tetrahydropyran-2-yloxy)(5S,7S,1R,6R)-2-oxabicyclo[3.3.0]octan-3-one

Base Information

• Chemical Name: 6-{(1E)(3S)-3-(2H-3,4,5,6-tetrahydropyran-2-yloxy)-4-[3-(methoxymethyl)phenyl]but-1-enyl}-7-(2H-3,4,5,6-tetrahydropyran-2-yloxy)(5S,7S,1R,6R)-2-oxabicyclo[3.3.0]octan-3-one
• CAS No.: 256382-42-0
• Molecular Formula: C₂₉H₄₀O₇
• Molecular Weight: 500.632

Synonyms:6-{(1E)(3S)-3-(2H-3,4,5,6-tetrahydropyran-2-yloxy)-4-[3-(methoxymethyl)phenyl]but-1-enyl}-7-(2H-3,4,5,6-tetrahydropyran-2-yloxy)(5S,7S,1R,6R)-2-oxabicyclo[3.3.0]octan-3-one

Chemical Property of 6-{(1E)(3S)-3-(2H-3,4,5,6-tetrahydropyran-2-yloxy)-4-[3-(methoxymethyl)phenyl]but-1-enyl}-7-(2H-3,4,5,6-tetrahydropyran-2-yloxy)(5S,7S,1R,6R)-2-oxabicyclo[3.3.0]octan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 6-{(1E)(3S)-3-(2H-3,4,5,6-tetrahydropyran-2-yloxy)-4-[3-(methoxymethyl)phenyl]but-1-enyl}-7-(2H-3,4,5,6-tetrahydropyran-2-yloxy)(5S,7S,1R,6R)-2-oxabicyclo[3.3.0]octan-3-one

There total 5 articles about 6-{(1E)(3S)-3-(2H-3,4,5,6-tetrahydropyran-2-yloxy)-4-[3-(methoxymethyl)phenyl]but-1-enyl}-7-(2H-3,4,5,6-tetrahydropyran-2-yloxy)(5S,7S,1R,6R)-2-oxabicyclo[3.3.0]octan-3-one 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:

3,4-dihydro-2H-pyran (110-87-2) + p-toluenesulfonic acid monohydrate (6192-52-5) + 6-{(1E)(3S)-3-hydroxy-4-[3-(methoxymethyl)phenyl]but-1-enyl}-7-(2H-3,4,5,6-tetrahydropyran-2-yloxy)(5S,7S,1R,6R)-2-oxabicyclo[3.3.0]octan-3-one (256382-41-9) → 6-{(1E)(3S)-3-(2H-3,4,5,6-tetrahydropyran-2-yloxy)-4-[3-(methoxymethyl)phenyl]but-1-enyl}-7-(2H-3,4,5,6-tetrahydropyran-2-yloxy)(5S,7S,1R,6R)-2-oxabicyclo[3.3.0]octan-3-one (256382-42-0)

Guidance literature:

With triethylamine; In dichloromethane;

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) + 6-{(1E)(3S)-3-hydroxy-4-[3-(methoxymethyl)phenyl]but-1-enyl}-7-(2H-3,4,5,6-tetrahydropyran-2-yloxy)(5S,7S,1R,6R)-2-oxabicyclo[3.3.0]octan-3-one (256382-41-9) → 6-{(1E)(3S)-3-(2H-3,4,5,6-tetrahydropyran-2-yloxy)-4-[3-(methoxymethyl)phenyl]but-1-enyl}-7-(2H-3,4,5,6-tetrahydropyran-2-yloxy)(5S,7S,1R,6R)-2-oxabicyclo[3.3.0]octan-3-one (256382-42-0)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; toluene; at 20 ℃; for 0.75h;

DOI:10.1016/S0968-0896(02)00085-8

Reference yield:

2-oxo-6-syn-(hydroxymethyl)-7-anti-(tetrahydropyran-2-yloxy)-cis-bicyclo<3.3.0>octan-3-one (69222-61-3) → 6-{(1E)(3S)-3-(2H-3,4,5,6-tetrahydropyran-2-yloxy)-4-[3-(methoxymethyl)phenyl]but-1-enyl}-7-(2H-3,4,5,6-tetrahydropyran-2-yloxy)(5S,7S,1R,6R)-2-oxabicyclo[3.3.0]octan-3-one (256382-42-0)

Guidance literature:

Multi-step reaction with 4 steps

1: SO₃*Py; Et₃N / ethyl acetate; dimethylsulfoxide / 1 h / cooling

2: 83.1 percent / NaH / tetrahydrofuran / 0.5 h / 20 °C

3: LiAlH₄; (S)-BINOL / tetrahydrofuran; ethanol / 2 h / cooling

4: para-toluenesulfonic acid monohydrate / toluene; tetrahydrofuran / 0.75 h / 20 °C

With lithium aluminium tetrahydride; pyridine-SO₃ complex; (S)-[1,1']-binaphthalenyl-2,2'-diol; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; ethanol; dimethyl sulfoxide; ethyl acetate; toluene; 2: Horner-Emmons reaction;

DOI:10.1016/S0968-0896(02)00085-8

upstream raw materials:

3,4-dihydro-2H-pyran

6-{(1E)(3S)-3-hydroxy-4-[3-(methoxymethyl)phenyl]but-1-enyl}-7-(2H-3,4,5,6-tetrahydropyran-2-yloxy)(5S,7S,1R,6R)-2-oxabicyclo[3.3.0]octan-3-one

2-oxo-6-syn-(hydroxymethyl)-7-anti-(tetrahydropyran-2-yloxy)-cis-bicyclo<3.3.0>octan-3-one

(3aR,4R,5R,6aS)-hexahydro-2-oxo-5-<(tetrahydro-2H-pyran-2-yl)oxy>-2H-cyclopentafuran-4-carboxaldehyde

Downstream raw materials:

11(R),15(S)-bis(tetrahydro-2-pyranyloxy)-5,9(S)-dihydroxy-16-(3-methoxymethyl)phenyl-1,2,3,4,17,18,19,20-octanorprostanoic acid

5-thia-16-(3-methoxymethylphenyl)methylPGE₁

Rivenprost

16-(3-methoxymethyl)phenyl-ω-tetranor-5-thiaprostaglandin F₁ methyl ester 11,15-bis(tetrahydropyran-2-yl ether)

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