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

Base Information

• Chemical Name: 16-(3-methoxymethyl)phenyl-ω-tetranor-5-thiaprostaglandin E₁ methyl ester 11,15-bis(tetrahydropyran-2-yl ether)
• CAS No.: 256382-46-4
• Molecular Formula: C₃₄H₅₀O₈S
• Molecular Weight: 618.832
• Mol file: 256382-46-4.mol

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

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

There total 9 articles about 16-(3-methoxymethyl)phenyl-ω-tetranor-5-thiaprostaglandin E₁ 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: 90.7%

16-(3-methoxymethyl)phenyl-ω-tetranor-5-thiaprostaglandin F1 methyl ester 11,15-bis(tetrahydropyran-2-yl ether) (256382-45-3) → 16-(3-methoxymethyl)phenyl-ω-tetranor-5-thiaprostaglandin E1 methyl ester 11,15-bis(tetrahydropyran-2-yl ether) (256382-46-4)

Guidance literature:

With pyridine-SO₃ complex; N-ethyl-N,N-diisopropylamine; In dimethyl sulfoxide; ethyl acetate; for 0.833333h; cooling;

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 E1 methyl ester 11,15-bis(tetrahydropyran-2-yl ether) (256382-46-4)

Guidance literature:

Multi-step reaction with 7 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

7: 90.7 percent / SO₃*Py; i-Pr₂NEt / ethyl acetate; dimethylsulfoxide / 0.83 h / cooling

With lithium aluminium tetrahydride; pyridine-SO₃ complex; potassium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dimethyl sulfoxide; ethyl acetate; 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 E1 methyl ester 11,15-bis(tetrahydropyran-2-yl ether) (256382-46-4)

Guidance literature:

Multi-step reaction with 10 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

10: 90.7 percent / SO₃*Py; i-Pr₂NEt / ethyl acetate; dimethylsulfoxide / 0.83 h / cooling

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:

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

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:

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

Rivenprost