Prostaglandin D-M

Base Information

• Chemical Name: Prostaglandin D-M
• CAS No.: 70803-92-8
• Molecular Formula: C₁₆H₂₂O₇
• Molecular Weight: 326.346
• Mol file: 70803-92-8.mol

Synonyms:9-HDTPD;9-hydroxy-11,15-dioxo-2,3,18,19-tetranorprost-5-ene-1,20-dioic acid;PGD-M;prostaglandin D-M

Chemical Property of Prostaglandin D-M

Chemical Property:

• Vapor Pressure: 2.19E-17mmHg at 25°C
• Boiling Point: 609.2°C at 760 mmHg
• Flash Point: 336.3°C
• PSA: 128.97000
• Density: 1.29g/cm³
• LogP: 1.18760
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 326.13655304
• Heavy Atom Count: 23
• Complexity: 495

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C1=O)CCC(=O)CCC(=O)O)CC=CCC(=O)O)O
• Isomeric SMILES: C1[C@@H]([C@@H]([C@H](C1=O)CCC(=O)CCC(=O)O)C/C=C\CC(=O)O)O

Technology Process of Prostaglandin D-M

There total 15 articles about Prostaglandin D-M 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: 75.0%

6-[(6R,7R,8S)-7-((Z)-4-Carboxy-but-2-enyl)-8-hydroxy-1,4-dithia-spiro[4.4]non-6-yl]-4-oxo-hexanoic acid (84800-81-7) → 6-[(1R,2R,3S)-2-((Z)-4-Carboxy-but-2-enyl)-3-hydroxy-5-oxo-cyclopentyl]-4-oxo-hexanoic acid (70803-92-8)

Guidance literature:

With calcium carbonate; mercury dichloride; In water; acetonitrile; at 23 ℃; for 8h;

DOI:10.1021/ja00344a047

Reference yield:

(1S,5R,6R,7R)-(-)-2-oxa-6-(hydroxymethyl)-7-acetoxybicyclo<3.3.0>-octan-3-one (26054-65-9) → 6-[(1R,2R,3S)-2-((Z)-4-Carboxy-but-2-enyl)-3-hydroxy-5-oxo-cyclopentyl]-4-oxo-hexanoic acid (70803-92-8)

Guidance literature:

Multi-step reaction with 14 steps

1: 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h / 0 °C

2: K₂CO₃ / methanol / 1.5 h / 23 °C

3: 90 percent / diisopropylcarbodiimide, dichloroacetic acid / benzene; dimethylsulfoxide / 0.5 h / 23 °C

4: zinc triflate / CH₂Cl₂ / 5 h / 23 °C

5: diisobutylaluminum hydride / toluene / 0.5 h / -78 °C

6: 90 percent / 1.) dimsyl sodium / 2.) DMSO, 25 deg C, 4 h

7: 75 percent / pyridine / CH₂Cl₂ / 4 h / 23 °C

8: tetra-n-butylammonium fluoride / tetrahydrofuran / 9 h / 50 °C

9: 95 percent / diisopropylcarbodiimide, dichloroacetic acid / benzene; dimethylsulfoxide / 0.5 h / 23 °C

10: 75 percent / tetrahydrofuran / 2 h / 23 °C

11: H₂S, K₂CO₃ / dimethylsulfoxide / 1 h / 23 °C

12: 65 percent / tri-n-butylphosphine / benzene / 7 h / 23 °C / Irradiation

13: 1.) H₂SO₄, 2.) 1 N NaOH / 1.) MeOH, 23 deg C, 5 min, 2.) MeOH-H₂O, 23 deg C, 10 h

14: 75 percent / mercuric chloride, CaCO₃ / acetonitrile; H₂O / 8 h / 23 °C

With pyridine; dichloro-acetic acid; dmap; sodium hydroxide; tributylphosphine; sulfuric acid; hydrogen sulfide; tetrabutyl ammonium fluoride; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; sodium methylsulfinylmethanide; potassium carbonate; calcium carbonate; mercury dichloride; diisopropyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; toluene; acetonitrile; benzene;

DOI:10.1021/ja00344a047

Reference yield:

(3aα,4α,5β,6aα)-(-)-5-acetoxyhexahydro-4-(methoxymethyl)-2H-cyclopentafuran-2-one (56487-71-9) → 6-[(1R,2R,3S)-2-((Z)-4-Carboxy-but-2-enyl)-3-hydroxy-5-oxo-cyclopentyl]-4-oxo-hexanoic acid (70803-92-8)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) trimethylchlorosilane, NaI / 1.) MeCN, 50 deg C, 4 h

2: 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h / 0 °C

3: K₂CO₃ / methanol / 1.5 h / 23 °C

4: 90 percent / diisopropylcarbodiimide, dichloroacetic acid / benzene; dimethylsulfoxide / 0.5 h / 23 °C

5: zinc triflate / CH₂Cl₂ / 5 h / 23 °C

6: diisobutylaluminum hydride / toluene / 0.5 h / -78 °C

7: 90 percent / 1.) dimsyl sodium / 2.) DMSO, 25 deg C, 4 h

8: 75 percent / pyridine / CH₂Cl₂ / 4 h / 23 °C

9: tetra-n-butylammonium fluoride / tetrahydrofuran / 9 h / 50 °C

10: 95 percent / diisopropylcarbodiimide, dichloroacetic acid / benzene; dimethylsulfoxide / 0.5 h / 23 °C

11: 75 percent / tetrahydrofuran / 2 h / 23 °C

12: H₂S, K₂CO₃ / dimethylsulfoxide / 1 h / 23 °C

13: 65 percent / tri-n-butylphosphine / benzene / 7 h / 23 °C / Irradiation

14: 1.) H₂SO₄, 2.) 1 N NaOH / 1.) MeOH, 23 deg C, 5 min, 2.) MeOH-H₂O, 23 deg C, 10 h

15: 75 percent / mercuric chloride, CaCO₃ / acetonitrile; H₂O / 8 h / 23 °C

With pyridine; dichloro-acetic acid; dmap; sodium hydroxide; chloro-trimethyl-silane; tributylphosphine; sulfuric acid; hydrogen sulfide; tetrabutyl ammonium fluoride; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; sodium methylsulfinylmethanide; potassium carbonate; calcium carbonate; sodium iodide; mercury dichloride; diisopropyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; toluene; acetonitrile; benzene;

DOI:10.1021/ja00344a047

upstream raw materials:

6-[(6R,7R,8S)-7-((Z)-4-Carboxy-but-2-enyl)-8-hydroxy-1,4-dithia-spiro[4.4]non-6-yl]-4-oxo-hexanoic acid

(1S,5R,6R,7R)-(-)-2-oxa-6-(hydroxymethyl)-7-acetoxybicyclo<3.3.0>-octan-3-one

(3aα,4α,5β,6aα)-(-)-5-acetoxyhexahydro-4-(methoxymethyl)-2H-cyclopentafuran-2-one

(3aR,4S,5R,6aS)-hexahydro-5-hydroxy-4-[(tert-butyldiphenylsilyloxy)methyl]-2H-cyclopenta[b]furan-2-one

Refernces