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

Base Information

• Chemical Name: 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
• CAS No.: 256382-41-9
• Molecular Formula: C₂₄H₃₂O₆
• Molecular Weight: 416.514

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of 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

There total 4 articles about 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 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:

sodium hydrogen tartrate + (1S,5R,6R,7R)-3-oxo-6-(4-(3-methoxymethylphenyl)-3-oxo-1-butenyl)-7-(2-tetrahydropyranyloxy)-2-oxabicyclo[3.3.0]octane + ethyl acetate n-hexane + 2,2'-binaphthol (604-60-4,122531-87-7,122531-88-8) → 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)

Guidance literature:

With sodium chloride; In tetrahydrofuran; methanol; ethanol;

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-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)

Guidance literature:

Multi-step reaction with 3 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

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

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

Reference yield:

(3aR,4R,5R,6aS)-hexahydro-2-oxo-5-<(tetrahydro-2H-pyran-2-yl)oxy>-2H-cyclopentafuran-4-carboxaldehyde (32233-41-3) → 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)

Guidance literature:

Multi-step reaction with 2 steps

1: 83.1 percent / NaH / tetrahydrofuran / 0.5 h / 20 °C

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

With lithium aluminium tetrahydride; (S)-[1,1']-binaphthalenyl-2,2'-diol; sodium hydride; In tetrahydrofuran; ethanol; 1: Horner-Emmons reaction;

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

upstream raw materials:

6-{(1E)-4-[3-(methoxymethyl)phenyl]-3-oxobut-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

2,2'-binaphthol

Downstream raw materials:

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

16-(3-methoxymethyl)phenyl-ω-tetranor-5-thiaprostaglandin E₁ methyl ester 11,15-bis(tetrahydropyran-2-yl ether)

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

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

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