TETRANOR-PGDM

Base Information

• Chemical Name: TETRANOR-PGDM
• CAS No.: 133161-96-3
• Molecular Formula: C₁₆H₂₄O₇
• Molecular Weight: 328.362
• Mol file: 133161-96-3.mol

Synonyms:TETRANOR-PGDM;TETRANOR-PROSTAGLANDIN D METABOLITE;PGDM

Chemical Property of TETRANOR-PGDM

Chemical Property:

• PSA: 132.13000
• LogP: 0.97940

Purity/Quality:

98%Min ^*data from raw suppliers

PGD-M ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Prostaglandin D2 (PGD2) plays a pharmacological role in allergic and asthmatic anaphylaxis, normal physiological sleep and lowering of body temperature, as well as inhibits platelet aggregation and relaxes vascular smooth muscle. PGDM is a major urinary metabolite of PGD2 with a unique lower sidechain that readily undergoes reversible cyclization. It is used as a biomarker to assess endogenous production of PGD2.
• Uses: Labelled PGD-M Prostaglandin D2 (PGD2) plays a pharmacological role in allergic and asthmatic anaphylaxis, normal physiological sleep and lowering of body temperature, as well as inhibits platelet aggregation and relaxes vascular smooth muscle. PGDM is a major urinary metabolite of PGD2 with a unique lower sidechain that readily undergoes reversible cyclization. It is used as a biomarker to assess endogenous production of PGD2. PGD-M is the major urinary metabolite of PGD2 in humans.

Technology Process of TETRANOR-PGDM

There total 32 articles about TETRANOR-PGDM 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:

(-)-Corey lactone 5-(4-phenylbenzoate) (31752-99-5) → (Z)-9α-11β-dihydroxy-15-oxo-2,3,18.19-tetranorprost-5-ene-1,20-dioic acid (133161-96-3)

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) dicyclohexylcarbodi-imide; 2.) dichloroacetic acid; 3.) oxalic acid / 1.) benzene, DMSO, 5 min; 2.) 20 min, 3.) methanol, 10 min

2: tetrahydrofuran / 3 h / Ambient temperature

3: 90 percent / H₂ / palladium-carbon / ethyl acetate / 4 h / Ambient temperature

4: 82 percent / zinc triflate / CH₂Cl₂ / 2 h / Ambient temperature

5: 88 percent / t-BuOK / methanol; methyl acetate / 2 h / Ambient temperature

6: 70 percent / toluene-p-sulphonic acid / CH₂Cl₂ / 1 h / Ambient temperature

7: 92 percent / DIBAL / tetrahydrofuran / 0.5 h / -78 °C

8: 1.) lithium bis(trimethylsilyl)amide / 1.) THF-HMPA, 0 deg C, 30 min; 2.) -40 to 0 deg C, THF, 30 min then 0 deg C, 2 h

9: 1.) NaHSO₄; 2.) LiOH / 1.) water, DME, pH 3, 0 deg C, 20 min; 2.) water, RT, 1 h

10: tetramethylammonium hydroxide / dimethylformamide / 0.33 h / 0 °C

11: 80 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

12: 88 percent / cation exchange resin AG₅₀-X₈ / methanol / 6 h / 23 °C

13: triethylamine / CH₂Cl₂ / 0.5 h / -20 °C

14: 18-crown-6-ether / toluene / 8 h / 115 °C / Heating

15: 70 percent / ceric ammonium nitrate / acetonitrile; H₂O / 1 h / Ambient temperature

16: LiOH / 1,2-dimethoxy-ethane; H₂O / 1 h / Ambient temperature

With pyridine; dichloro-acetic acid; lithium hydroxide; sodium hydrogen sulfate; ammonium cerium(IV) nitrate; 18-crown-6 ether; cation exchange resin AG₅₀-X₈; potassium tert-butylate; tetramethyl ammoniumhydroxide; hydrogen; oxalic acid; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; triethylamine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; palladium on activated charcoal; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; acetic acid methyl ester; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1039/P19880002821

Reference yield:

(-)-Corey lactone 5-(4-phenylbenzoate) (31752-99-5) → 6-[(1R,2R,3S,5S)-2-((E)-4-Carboxy-but-2-enyl)-3,5-dihydroxy-cyclopentyl]-4-oxo-hexanoic acid (34069-64-2,99437-87-3,133161-96-3)

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) dicyclohexylcarbodi-imide; 2.) dichloroacetic acid; 3.) oxalic acid / 1.) benzene, DMSO, 5 min; 2.) 20 min, 3.) methanol, 10 min

2: tetrahydrofuran / 3 h / Ambient temperature

3: 90 percent / H₂ / palladium-carbon / ethyl acetate / 4 h / Ambient temperature

4: 82 percent / zinc triflate / CH₂Cl₂ / 2 h / Ambient temperature

5: 88 percent / t-BuOK / methanol; methyl acetate / 2 h / Ambient temperature

6: 70 percent / toluene-p-sulphonic acid / CH₂Cl₂ / 1 h / Ambient temperature

7: 92 percent / DIBAL / tetrahydrofuran / 0.5 h / -78 °C

8: 1.) lithium bis(trimethylsilyl)amide / 1.) THF-HMPA, 0 deg C, 30 min; 2.) -40 to 0 deg C, THF, 30 min then 0 deg C, 2 h

9: 1.) NaHSO₄; 2.) LiOH / 1.) water, DME, pH 3, 0 deg C, 20 min; 2.) water, RT, 1 h

10: tetramethylammonium hydroxide / dimethylformamide / 0.33 h / 0 °C

11: pyridine / CH₂Cl₂ / 0.5 h / 0 °C

12: cation exchange resin AG₅₀-X₈ / methanol / 6 h / 23 °C

13: triethylamine / CH₂Cl₂ / 0.5 h / -20 °C

14: 18-crown-6-ether / toluene / 8 h / 115 °C / Heating

15: ceric ammonium nitrate / acetonitrile; H₂O / 1 h / Ambient temperature

16: LiOH / 1,2-dimethoxy-ethane; H₂O / 1 h / Ambient temperature

With pyridine; dichloro-acetic acid; lithium hydroxide; sodium hydrogen sulfate; ammonium cerium(IV) nitrate; 18-crown-6 ether; cation exchange resin AG₅₀-X₈; potassium tert-butylate; tetramethyl ammoniumhydroxide; hydrogen; oxalic acid; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; triethylamine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; palladium on activated charcoal; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; acetic acid methyl ester; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1039/P19880002821

Reference yield:

3-{2-[2-((3aR,4R,5R,6aS)-5-Hydroxy-2-oxo-hexahydro-cyclopenta[b]furan-4-yl)-ethyl]-[1,3]dithiolan-2-yl}-propionic acid methyl ester (118908-19-3) → (Z)-9α-11β-dihydroxy-15-oxo-2,3,18.19-tetranorprost-5-ene-1,20-dioic acid (133161-96-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 70 percent / toluene-p-sulphonic acid / CH₂Cl₂ / 1 h / Ambient temperature

2: 92 percent / DIBAL / tetrahydrofuran / 0.5 h / -78 °C

3: 1.) lithium bis(trimethylsilyl)amide / 1.) THF-HMPA, 0 deg C, 30 min; 2.) -40 to 0 deg C, THF, 30 min then 0 deg C, 2 h

4: 1.) NaHSO₄; 2.) LiOH / 1.) water, DME, pH 3, 0 deg C, 20 min; 2.) water, RT, 1 h

5: tetramethylammonium hydroxide / dimethylformamide / 0.33 h / 0 °C

6: 80 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

7: 88 percent / cation exchange resin AG₅₀-X₈ / methanol / 6 h / 23 °C

8: triethylamine / CH₂Cl₂ / 0.5 h / -20 °C

9: 18-crown-6-ether / toluene / 8 h / 115 °C / Heating

10: 70 percent / ceric ammonium nitrate / acetonitrile; H₂O / 1 h / Ambient temperature

11: LiOH / 1,2-dimethoxy-ethane; H₂O / 1 h / Ambient temperature

With pyridine; lithium hydroxide; sodium hydrogen sulfate; ammonium cerium(IV) nitrate; 18-crown-6 ether; cation exchange resin AG₅₀-X₈; tetramethyl ammoniumhydroxide; diisobutylaluminium hydride; triethylamine; lithium hexamethyldisilazane; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1039/P19880002821

upstream raw materials:

6-[(1R,2R,3S,5S)-3,5-Diacetoxy-2-((Z)-4-methoxycarbonyl-but-2-enyl)-cyclopentyl]-4-oxo-hexanoic acid methyl ester

(-)-Corey lactone 5-(4-phenylbenzoate)

3-{2-[2-((3aR,4R,5R,6aS)-5-Hydroxy-2-oxo-hexahydro-cyclopenta[b]furan-4-yl)-ethyl]-[1,3]dithiolan-2-yl}-propionic acid methyl ester

3-(2-{2-[(3aR,4R,5R,6aS)-2-Hydroxy-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-4-yl]-ethyl}-[1,3]dithiolan-2-yl)-propionic acid methyl ester