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

Base Information

• Chemical Name: 16-(4-chlorophenoxy)-17,18,19,20-tetranorprostaglandin F_2α 9-acetate methyl ester 11-(tetrahydropyran-2-yl ether)
• CAS No.: 62561-54-0
• Molecular Formula: C₃₀H₄₁ClO₈
• Molecular Weight: 565.104

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

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

Chemical Property:

Purity/Quality:

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

There total 7 articles about 16-(4-chlorophenoxy)-17,18,19,20-tetranorprostaglandin 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:

16-(3-chlorophenoxy)-17,18,19,20-tetranor-15-dehydroprostaglandin F2α 9-acetate methyl ester 11-(tetrahydropyran-2-yl ether) (62524-96-3) → (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 (62524-97-4) + 16-(4-chlorophenoxy)-17,18,19,20-tetranorprostaglandin F2α 9-acetate methyl ester 11-(tetrahydropyran-2-yl ether) (62561-54-0)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -45 ℃; Yield given. Yields of byproduct given;

DOI:10.1021/jm00179a011

Reference yield:

dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate (40665-94-9) → 16-(4-chlorophenoxy)-17,18,19,20-tetranorprostaglandin F2α 9-acetate methyl ester 11-(tetrahydropyran-2-yl ether) (62561-54-0)

Guidance literature:

Multi-step reaction with 2 steps

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

2: NaBH₄ / methanol; tetrahydrofuran / -45 °C

With sodium tetrahydroborate; sodium hydride; In tetrahydrofuran; methanol;

DOI:10.1021/jm00179a011

Reference yield:

methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate (61218-06-2) → 16-(4-chlorophenoxy)-17,18,19,20-tetranorprostaglandin F2α 9-acetate methyl ester 11-(tetrahydropyran-2-yl ether) (62561-54-0)

Guidance literature:

Multi-step reaction with 2 steps

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

2: NaBH₄ / methanol; tetrahydrofuran / -45 °C

With sodium tetrahydroborate; sodium hydride; In tetrahydrofuran; methanol;

DOI:10.1021/jm00179a011

upstream raw materials:

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

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

Downstream raw materials:

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

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

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

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