11-DEOXY PROSTAGLANDIN E2

Base Information

• Chemical Name: 11-DEOXY PROSTAGLANDIN E2
• CAS No.: 35536-53-9
• Molecular Formula: C20H32 O4
• Molecular Weight: 336.472
• Mol file: 35536-53-9.mol

Synonyms:11-Deoxy-PGE2;11-Deoxyprostaglandin E2; 15(S)-Hydroxy-9-oxoprosta-5-cis-13-trans-dienoicacid; 15a-Hydroxy-9-keto-prosta-5,13-dienoicacid; Wy 18189; ZK 73-466

Chemical Property of 11-DEOXY PROSTAGLANDIN E2

Chemical Property:

• PSA: 74.60000
• LogP: 4.28030

Purity/Quality:

99%,98%, ^*data from raw suppliers

11-deoxy Prostaglandin E2 ≥99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: 11-deoxy Prostaglandin E2 (11-deoxy PGE2) is a stable, synthetic analog of PGE2 . In contrast to PGE2 which has bronchodilation effects, 11-deoxy PGE2 is a powerful bronchoconstrictor and contracts human respiratory tract smooth muscle with potencies ranging from 5 to 30 times higher than PGF2α .

Technology Process of 11-DEOXY PROSTAGLANDIN E2

There total 32 articles about 11-DEOXY PROSTAGLANDIN E2 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:

(Z)-7-[(1S,2R)-2-((E)-(S)-3-Hydroxy-oct-1-enyl)-5-oxo-cyclopentyl]-hept-5-enoic acid methyl ester (35120-22-0,37794-69-7,38698-63-4,41300-47-4,51819-56-8,52153-14-7,52520-73-7,53495-10-6,58342-12-4,58342-13-5,110269-85-7) → rac-8R*,9S*,12S*,15R*-11-deoxyprostaglandin-E2 (35183-82-5,35536-53-9,41300-68-9,41502-76-5,52153-12-5,58342-14-6,58342-15-7,59014-31-2,61376-55-4)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 72h; Yield given;

Reference yield:

(6S,7S)-6-Formyl-1,4-dioxa-spiro[4.4]nonane-7-carboxylic acid isopropyl ester (90157-52-1) → 11-deoxy-PGE2 (35183-82-5,35536-53-9,41300-68-9,41502-76-5,52153-12-5,58342-14-6,58342-15-7,59014-31-2,61376-55-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / toluene; tetrahydrofuran / 0 °C

2: 1.) DIBAH / 1.) -78 deg C, toluene, 1 h; 2.) THF

3: 1.) NaBH₄; 2.) Hg(OAc)2 / 1.) MeOH; 2.) THF-H₂O

4: 2.) acetic acid-water / 1.) DMSO

With sodium tetrahydroborate; mercury(II) diacetate; diisobutylaluminium hydride; acetic acid; In tetrahydrofuran; toluene;

DOI:10.1016/S0040-4039(00)99968-4

Reference yield:

2-[2-Isopropoxycarbonyl-eth-(E)-ylidene]-3-oxo-cyclopentanecarboxylic acid isopropyl ester (90157-49-6,90157-50-9) → 11-deoxy-PGE2 (35183-82-5,35536-53-9,41300-68-9,41502-76-5,52153-12-5,58342-14-6,58342-15-7,59014-31-2,61376-55-4)

Guidance literature:

Multi-step reaction with 6 steps

2: 87 percent / NaIO₄-OsO₄

3: 84 percent / toluene; tetrahydrofuran / 0 °C

4: 1.) DIBAH / 1.) -78 deg C, toluene, 1 h; 2.) THF

5: 1.) NaBH₄; 2.) Hg(OAc)2 / 1.) MeOH; 2.) THF-H₂O

6: 2.) acetic acid-water / 1.) DMSO

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; mercury(II) diacetate; diisobutylaluminium hydride; acetic acid; In tetrahydrofuran; toluene;

DOI:10.1016/S0040-4039(00)99968-4

upstream raw materials:

5-(Triphenyl-λ⁵-phosphanylidene)-pentanoic acid anion

[(6R,7R)-7-((E)-(S)-3-Hydroxy-oct-1-enyl)-1,4-dioxa-spiro[4.4]non-6-yl]-acetaldehyde

γ-lactone of 5α-hydroxy-2β-(3-oxo-1-trans-octenyl)-1α-cyclopentaneacetic acid

(3aR,4R,6aS)-4-((E)-3-Hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-2-one