16-(3-chlorophenoxy)-17,18,19,20-tetranor-15-dehydroprostaglandin F_2α 9-acetate methyl ester 11-(tetrahydropyran-2-yl ether)

Base Information

• Chemical Name: 16-(3-chlorophenoxy)-17,18,19,20-tetranor-15-dehydroprostaglandin F_2α 9-acetate methyl ester 11-(tetrahydropyran-2-yl ether)
• CAS No.: 62524-96-3
• Molecular Formula: C₃₀H₃₉ClO₈
• Molecular Weight: 563.088

Synonyms:16-(3-chlorophenoxy)-17,18,19,20-tetranor-15-dehydroprostaglandin F_2α 9-acetate methyl ester 11-(tetrahydropyran-2-yl ether)

Chemical Property of 16-(3-chlorophenoxy)-17,18,19,20-tetranor-15-dehydroprostaglandin F_2α 9-acetate methyl ester 11-(tetrahydropyran-2-yl ether)

Chemical Property:

Purity/Quality:

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Technology Process of 16-(3-chlorophenoxy)-17,18,19,20-tetranor-15-dehydroprostaglandin F_2α 9-acetate methyl ester 11-(tetrahydropyran-2-yl ether)

There total 5 articles about 16-(3-chlorophenoxy)-17,18,19,20-tetranor-15-dehydroprostaglandin F_2α 9-acetate methyl ester 11-(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 (5Z)-7-{(1R,2S,3R,5R)-5-acetoxy-2-hydroxymethyl-3-[(2-oxacyclohexyl)oxy]-cyclopentyl}-5-heptenoate (61218-10-8) → 16-(3-chlorophenoxy)-17,18,19,20-tetranor-15-dehydroprostaglandin F2α 9-acetate methyl ester 11-(tetrahydropyran-2-yl ether) (62524-96-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / SO₃-pyridine complex, Et₃N / dimethylsulfoxide / 0.25 h / 20 °C

2: 1.) NaH / 1.) THF, 25 deg C, 20 min, 2.) THF, from 25 deg C to 60 deg C, 4.5 h

With pyridine-SO₃ complex; sodium hydride; triethylamine; In dimethyl sulfoxide;

DOI:10.1021/jm00179a011

Reference yield:

2-syn-(6-carbomethoxy2-cis-hexenyl)-3-anti-(2,4-dioxa-3,3dimethylpentyl)-4-syn-(tetrahydropyran-2-yloxy)cyclopentan-1-ol (69810-09-9) → 16-(3-chlorophenoxy)-17,18,19,20-tetranor-15-dehydroprostaglandin F2α 9-acetate methyl ester 11-(tetrahydropyran-2-yl ether) (62524-96-3)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 15 h / 20 °C

2: 0.5 N aq. HCl / tetrahydrofuran / -5 °C

3: 90 percent / SO₃-pyridine complex, Et₃N / dimethylsulfoxide / 0.25 h / 20 °C

4: 1.) NaH / 1.) THF, 25 deg C, 20 min, 2.) THF, from 25 deg C to 60 deg C, 4.5 h

With pyridine; hydrogenchloride; pyridine-SO₃ complex; sodium hydride; triethylamine; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1021/jm00179a011

Reference yield:

(Z)-7-[(1R,2S,3R,5S)-5-Acetoxy-2-(1-methoxy-1-methyl-ethoxymethyl)-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester (102276-55-1) → 16-(3-chlorophenoxy)-17,18,19,20-tetranor-15-dehydroprostaglandin F2α 9-acetate methyl ester 11-(tetrahydropyran-2-yl ether) (62524-96-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 0.5 N aq. HCl / tetrahydrofuran / -5 °C

2: 90 percent / SO₃-pyridine complex, Et₃N / dimethylsulfoxide / 0.25 h / 20 °C

3: 1.) NaH / 1.) THF, 25 deg C, 20 min, 2.) THF, from 25 deg C to 60 deg C, 4.5 h

With hydrogenchloride; pyridine-SO₃ complex; sodium hydride; triethylamine; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1021/jm00179a011

upstream raw materials:

dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate

methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate

methyl (5Z)-7-{(1R,2S,3R,5R)-5-acetoxy-2-hydroxymethyl-3-[(2-oxacyclohexyl)oxy]-cyclopentyl}-5-heptenoate

2-syn-(6-carbomethoxy2-cis-hexenyl)-3-anti-(2,4-dioxa-3,3dimethylpentyl)-4-syn-(tetrahydropyran-2-yloxy)cyclopentan-1-ol

Downstream raw materials:

(Z)-7-[(1R,2R,3R,5S)-5-Acetoxy-2-[(E)-(S)-4-(3-chloro-phenoxy)-3-hydroxy-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester

16-(4-chlorophenoxy)-17,18,19,20-tetranorprostaglandin F_2α 9-acetate methyl ester 11-(tetrahydropyran-2-yl ether)

16-(3-chlorophenoxy)-17,18,19,20-tetranor-2,3-trans-didehydroprostaglandin F_2α methyl ester

16-(3-chlorophenoxy)-17,18,19,20-tetranor-3,4-trans-didehydroprostaglandin F_2α methyl ester

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