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

Base Information

• Chemical Name: 16-(3-methoxymethyl)phenyl-ω-tetranor-5-thiaprostaglandin F₁ methyl ester 11,15-bis(tetrahydropyran-2-yl ether)
• CAS No.: 256382-45-3
• Molecular Formula: C₃₄H₅₂O₈S
• Molecular Weight: 620.848

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about 16-(3-methoxymethyl)phenyl-ω-tetranor-5-thiaprostaglandin F₁ methyl ester 11,15-bis(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:

methyl 4-iodobutanoate (14273-85-9) + 11(R),15(S)-bis(tetrahydro-2-pyranyloxy)-16-(3-methoxymethyl)phenyl-1,2,3,4,17,18,19,20-octanor-5-acetylthio-9(S)-trimethylsilyloxyprostanoic acid → 16-(3-methoxymethyl)phenyl-ω-tetranor-5-thiaprostaglandin F1 methyl ester 11,15-bis(tetrahydropyran-2-yl ether) (256382-45-3)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 2h;

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

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → 16-(3-methoxymethyl)phenyl-ω-tetranor-5-thiaprostaglandin F1 methyl ester 11,15-bis(tetrahydropyran-2-yl ether) (256382-45-3)

Guidance literature:

Multi-step reaction with 6 steps

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

2: LiAlH₄ / tetrahydrofuran / 0.75 h / cooling

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

4: i-Pr₂NEt / tetrahydrofuran; methanol / 0.17 h / -10 - -5 °C

5: K₂CO₃ / tetrahydrofuran; methanol; dimethylformamide / 4 h / 50 °C

6: 10.5 g / K₂CO₃ / methanol / 2 h / 20 °C

With lithium aluminium tetrahydride; potassium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene;

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) → 16-(3-methoxymethyl)phenyl-ω-tetranor-5-thiaprostaglandin F1 methyl ester 11,15-bis(tetrahydropyran-2-yl ether) (256382-45-3)

Guidance literature:

Multi-step reaction with 9 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

5: LiAlH₄ / tetrahydrofuran / 0.75 h / cooling

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

7: i-Pr₂NEt / tetrahydrofuran; methanol / 0.17 h / -10 - -5 °C

8: K₂CO₃ / tetrahydrofuran; methanol; dimethylformamide / 4 h / 50 °C

9: 10.5 g / K₂CO₃ / methanol / 2 h / 20 °C

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

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

upstream raw materials:

methyl 4-iodobutanoate

3,4-dihydro-2H-pyran

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:

(9α,11α,15α,13E)-9-hydroxy-11,15-bis(tetrahydropyran-2-yloxy)-16-(3-methoxymethylphenyl)-17,18,19,20-tetranor-5-thiaprost-13-enoic acid

4-{2-[(1R,2R,3R,5R)-5-Fluoro-2-[(E)-(S)-4-(3-methoxymethyl-phenyl)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethylsulfanyl}-butyric acid methyl ester

4-(2-{(1R,2R,3R,5R)-5-Fluoro-3-hydroxy-2-[(E)-(S)-3-hydroxy-4-(3-methoxymethyl-phenyl)-but-1-enyl]-cyclopentyl}-ethylsulfanyl)-butyric acid methyl ester

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