(5Z,11α,13E)-16-Benzyl-18-cyan-11,15-dihydroxy-9-oxo-19,20-dinorprosta-5,13-dien-1-saeure

Base Information

Chemical Name:(5Z,11α,13E)-16-Benzyl-18-cyan-11,15-dihydroxy-9-oxo-19,20-dinorprosta-5,13-dien-1-saeure
CAS No.:81266-96-8
Molecular Formula:C₂₆H₃₃NO₅
Molecular Weight:439.552
Hs Code.:

Synonyms:(5Z,11α,13E)-16-Benzyl-18-cyan-11,15-dihydroxy-9-oxo-19,20-dinorprosta-5,13-dien-1-saeure

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Chemical Property of (5Z,11α,13E)-16-Benzyl-18-cyan-11,15-dihydroxy-9-oxo-19,20-dinorprosta-5,13-dien-1-saeure

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Technology Process of (5Z,11α,13E)-16-Benzyl-18-cyan-11,15-dihydroxy-9-oxo-19,20-dinorprosta-5,13-dien-1-saeure

There total 10 articles about (5Z,11α,13E)-16-Benzyl-18-cyan-11,15-dihydroxy-9-oxo-19,20-dinorprosta-5,13-dien-1-saeure 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: 41.0%

: 81266-93-5
(Z)-7-[(1R,3R)-2-[(E)-4-Benzyl-6-cyano-3-(tetrahydro-pyran-2-yloxy)-hex-1-enyl]-5-oxo-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid

: 81266-96-8
(5Z,11α,13E)-16-Benzyl-18-cyan-11,15-dihydroxy-9-oxo-19,20-dinorprosta-5,13-dien-1-saeure

Guidance literature:: In tetrahydrofuran; water; acetic acid; at 42 ℃; for 4h;
DOI:10.1002/jlac.198219820116

Reference yield:

: 81266-69-5
2-Benzyl-4-cyano-butyric acid methyl ester

: 81266-96-8
(5Z,11α,13E)-16-Benzyl-18-cyan-11,15-dihydroxy-9-oxo-19,20-dinorprosta-5,13-dien-1-saeure

Guidance literature:: Multi-step reaction with 9 steps

1: 1) 1,6 M BuLi / 1) THF, hexane, -78 deg C, 2) 7h, -78 deg C, 2h, 20 deg C

2: 1) 2,2 M BuLi / 1) THF, hexane, 2) 1,2-dimethoxyethane, 1h, 25 deg C

3: 98 percent / ZnCl₂, NaBH₄, / 1,2-dimethoxy-ethane / 1) 1,5 h, -20 deg C, 2) 1,5 h, 0 deg C, 3) 1,5 h, 20 deg C

4: 72 percent / K₂CO₃ / ethanol / 1.5 h / 25 °C

5: 90 percent / 2percent 4-toluoene sulfonic acid / CH₂Cl₂; tetrahydrofuran / 2 h / 20 °C

6: 100 percent / 70percent Na-dihydridobis(2-methoxyethoxy)aluminat / toluene / 6 h / -70 °C

7: 1) Na-bis(trimethylsilyl)amide / 1) DME, 1 h, 5-10 deg C, 2) 3 h, 25 deg C

8: CrO₃ / acetone; aq. H₂SO₄ / 3 h / -20 °C

9: 41 percent / acetic acid; H₂O; tetrahydrofuran / 4 h / 42 °C

With chromium(VI) oxide; sodium tetrahydroborate; n-butyllithium; sodium hexamethyldisilazane; potassium carbonate; toluene-4-sulfonic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; zinc(II) chloride; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; sulfuric acid; water; acetic acid; acetone; toluene;
DOI:10.1002/jlac.198219820116

Reference yield:

: 81266-72-0
4-Benzyl-6-dimethoxyphosphoryl-5-oxohexannitril

: 81266-96-8
(5Z,11α,13E)-16-Benzyl-18-cyan-11,15-dihydroxy-9-oxo-19,20-dinorprosta-5,13-dien-1-saeure

Guidance literature:: Multi-step reaction with 8 steps

1: 1) 2,2 M BuLi / 1) THF, hexane, 2) 1,2-dimethoxyethane, 1h, 25 deg C

2: 98 percent / ZnCl₂, NaBH₄, / 1,2-dimethoxy-ethane / 1) 1,5 h, -20 deg C, 2) 1,5 h, 0 deg C, 3) 1,5 h, 20 deg C

3: 72 percent / K₂CO₃ / ethanol / 1.5 h / 25 °C

4: 90 percent / 2percent 4-toluoene sulfonic acid / CH₂Cl₂; tetrahydrofuran / 2 h / 20 °C

5: 100 percent / 70percent Na-dihydridobis(2-methoxyethoxy)aluminat / toluene / 6 h / -70 °C

6: 1) Na-bis(trimethylsilyl)amide / 1) DME, 1 h, 5-10 deg C, 2) 3 h, 25 deg C

7: CrO₃ / acetone; aq. H₂SO₄ / 3 h / -20 °C

8: 41 percent / acetic acid; H₂O; tetrahydrofuran / 4 h / 42 °C

With chromium(VI) oxide; sodium tetrahydroborate; n-butyllithium; sodium hexamethyldisilazane; potassium carbonate; toluene-4-sulfonic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; zinc(II) chloride; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; sulfuric acid; water; acetic acid; acetone; toluene;
DOI:10.1002/jlac.198219820116