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

Base Information

• Chemical Name: 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
• CAS No.: 256382-40-8
• Molecular Formula: C₂₄H₃₀O₆
• Molecular Weight: 414.499

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 2 articles about 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 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: 83.1%

(3aR,4R,5R,6aS)-hexahydro-2-oxo-5-<(tetrahydro-2H-pyran-2-yl)oxy>-2H-cyclopentafuran-4-carboxaldehyde (32233-41-3) + {2-[(3-methoxymethyl-phenyl)methyl]-2-oxo-ethyl}phosphonic acid dimethyl ester (256382-39-5) → 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 (256382-40-8)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.5h;

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)-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 (256382-40-8)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With pyridine-SO₃ complex; sodium hydride; triethylamine; In tetrahydrofuran; dimethyl sulfoxide; ethyl acetate; 2: Horner-Emmons reaction;

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

Reference yield:

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 (256382-40-8) → Methanesulfonic acid 2-[(1R,2R,3R,5S)-5-hydroxy-2-[(E)-(S)-4-(3-methoxymethyl-phenyl)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethyl ester

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: LiAlH₄ / tetrahydrofuran / 0.75 h / cooling

4: i-Pr₂NEt / tetrahydrofuran / 0.5 h / -15 - -10 °C

With lithium aluminium tetrahydride; (S)-[1,1']-binaphthalenyl-2,2'-diol; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; toluene;

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

upstream raw materials:

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

{2-[(3-methoxymethyl-phenyl)methyl]-2-oxo-ethyl}phosphonic acid dimethyl ester

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

Downstream raw materials:

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

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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