rac-(15S)-9α,11α,15-trihydroxy-(8αH)-prost-13t-en-1-oic acid

Base Information

Chemical Name:rac-(15S)-9α,11α,15-trihydroxy-(8αH)-prost-13t-en-1-oic acid
CAS No.:42607-55-6
Molecular Formula:C₂₀H₃₆O₅
Molecular Weight:356.503
Hs Code.:

<i>rac</i>-(15<i>S</i>)-9α,11α,15-trihydroxy-(8α<i>H</i>)-prost-13<i>t</i>-en-1-oic acid

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of rac-(15S)-9α,11α,15-trihydroxy-(8αH)-prost-13t-en-1-oic acid

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Technology Process of rac-(15S)-9α,11α,15-trihydroxy-(8αH)-prost-13t-en-1-oic acid

There total 38 articles about rac-(15S)-9α,11α,15-trihydroxy-(8αH)-prost-13t-en-1-oic acid 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: 90.0%

: 71120-99-5,71121-00-1,72120-47-9
2β-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-3α-(6-carboxyhexyl)-1α,4α-dihydroxycyclopentanone

: 745-62-0,3613-66-9,10164-73-5,17066-90-9,20348-60-1,21562-54-9,26771-95-9,26771-96-0,34388-84-6,34388-86-8,34388-87-9,34388-89-1,34402-61-4,34437-28-0,37785-86-7,37818-61-4,42048-97-5,42587-03-1,42607-55-6,42607-56-7,54422-22-9,54422-23-0,55528-78-4,57759-92-9,57759-93-0,61375-87-9,61557-40-2,62860-86-0,62960-89-8
(+/-)-prostaglandin F1α

Guidance literature:: With hydrogen fluoride; In water; acetonitrile; for 1h; Ambient temperature;
DOI:10.1021/jo00231a014

Reference yield:

: 78823-20-8
trans-4-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-2,3-epoxycyclopentanone

: 745-62-0,3613-66-9,10164-73-5,17066-90-9,20348-60-1,21562-54-9,26771-95-9,26771-96-0,34388-84-6,34388-86-8,34388-87-9,34388-89-1,34402-61-4,34437-28-0,37785-86-7,37818-61-4,42048-97-5,42587-03-1,42607-55-6,42607-56-7,54422-22-9,54422-23-0,55528-78-4,57759-92-9,57759-93-0,61375-87-9,61557-40-2,62860-86-0,62960-89-8
(+/-)-prostaglandin F1α

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 1 h, 2.) THF, from -78 deg C to r.t., 6 h

2: 1.) CuCN / 1.) diethyl ether, -40 deg C, 1.5 h, 2.) ether, from -78 deg C to -10 deg C, overnight

3: KF, pH 7 phosphate buffer / ethanol / 3 h / Ambient temperature

4: 84 percent / L-selectride / tetrahydrofuran / 6 h / Ambient temperature

5: 75 percent / O₂ / PtO₂ / acetone; H₂O / 4 h / 40 °C

6: 90 percent / 47-52percent aq. HF / acetonitrile; H₂O / 1 h / Ambient temperature

With potassium fluoride; pH 7 phosphate buffer; hydrogen fluoride; oxygen; L-Selectride; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; ethanol; water; acetone; acetonitrile;
DOI:10.1021/jo00231a014

Reference yield:

: 93566-56-4,93711-56-9,110548-21-5
trans-4,5-epoxy-3-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-1-<(triethylsilyl)oxy>cyclopentene

: 745-62-0,3613-66-9,10164-73-5,17066-90-9,20348-60-1,21562-54-9,26771-95-9,26771-96-0,34388-84-6,34388-86-8,34388-87-9,34388-89-1,34402-61-4,34437-28-0,37785-86-7,37818-61-4,42048-97-5,42587-03-1,42607-55-6,42607-56-7,54422-22-9,54422-23-0,55528-78-4,57759-92-9,57759-93-0,61375-87-9,61557-40-2,62860-86-0,62960-89-8
(+/-)-prostaglandin F1α

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) CuCN / 1.) diethyl ether, -40 deg C, 1.5 h, 2.) ether, from -78 deg C to -10 deg C, overnight

2: KF, pH 7 phosphate buffer / ethanol / 3 h / Ambient temperature

3: 84 percent / L-selectride / tetrahydrofuran / 6 h / Ambient temperature

4: 75 percent / O₂ / PtO₂ / acetone; H₂O / 4 h / 40 °C

5: 90 percent / 47-52percent aq. HF / acetonitrile; H₂O / 1 h / Ambient temperature

With potassium fluoride; pH 7 phosphate buffer; hydrogen fluoride; oxygen; L-Selectride; platinum(IV) oxide; In tetrahydrofuran; ethanol; water; acetone; acetonitrile;
DOI:10.1021/jo00231a014