Tilsuprost

Base Information

• Chemical Name: Tilsuprost
• CAS No.: 75111-35-2
• Molecular Formula: C₂₀H₃₃NO₄S
• Molecular Weight: 383.552
• NCI Thesaurus Code: C76335
• Mol file: 75111-35-2.mol

Synonyms:beta-thia-imino-prostacyclin;HOE 892;HOE-892;S 79 2892 A

Chemical Property of Tilsuprost

Chemical Property:

• Vapor Pressure: 2.14E-12mmHg at 25°C
• Boiling Point: 506.9°C at 760 mmHg
• Flash Point: 260.3°C
• PSA: 104.42000
• Density: 1.22g/cm³
• LogP: 2.77360
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 383.21302971
• Heavy Atom Count: 26
• Complexity: 508

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC1C(CC2C1CC(=N2)SCCCC(=O)OC)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@H]2[C@@H]1CC(=N2)SCCCC(=O)OC)O)O

Technology Process of Tilsuprost

There total 26 articles about Tilsuprost 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:

(3aR,5R,6aS)-5-Hydroxy-4-(tetrahydro-pyran-2-yloxymethyl)-hexahydro-cyclopenta[b]furan-2-one (50703-26-9,62447-83-0,75172-26-8,88294-29-5) → 4-[(3aR,5R,6aS)-5-Hydroxy-4-((E)-3-hydroxy-oct-1-enyl)-3,3a,4,5,6,6a-hexahydro-cyclopenta[b]pyrrol-2-ylsulfanyl]-butyric acid methyl ester (75111-35-2,80184-98-1,80225-28-1,84893-57-2,84893-58-3)

Guidance literature:

Multi-step reaction with 15 steps

1: NaH / 50 °C

2: NH₃ / 36 h / 130 °C

3: CrO₃/H₂SO₄ / H₂O; acetone / -20 °C

4: ClSi(CH₃)3, pyridine / CH₂Cl₂ / Heating

5: Raney-Ni / 2-methyl-propan-2-ol / Ambient temperature

6: H₂ / Pd-C / methanol / 25 °C

7: pyridine / 5 °C

8: p-TsOH / methanol / 25 °C

9: DMSO, oxalylchloride / CH₂Cl₂ / -60 °C

10: NaH / 1,2-dimethoxy-ethane / 25 °C

11: ZnBH₄ / 1,2-dimethoxy-ethane / 25 °C

12: pyridine / 5 °C

13: P₄S₁₀*pyridine / pyridine / 80 °C

14: NaH / 1,2-dimethoxy-ethane / 25 °C

15: K₂CO₃ / methanol / 25 °C

With pyridine; chromium(VI) oxide; chloro-trimethyl-silane; zinc(II) tetrahydroborate; Chloro-oxo-acetic acid; P₂S₅-pyridine; sulfuric acid; ammonia; hydrogen; nickel; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; palladium on activated charcoal; In pyridine; methanol; 1,2-dimethoxyethane; dichloromethane; water; acetone; tert-butyl alcohol;

Reference yield:

(3aR,5R,6aS)-5-Benzyloxy-4-(tetrahydro-pyran-2-yloxymethyl)-hexahydro-cyclopenta[b]furan-2-one (75111-18-1,80184-30-1) → 4-[(3aR,5R,6aS)-5-Hydroxy-4-((E)-3-hydroxy-oct-1-enyl)-3,3a,4,5,6,6a-hexahydro-cyclopenta[b]pyrrol-2-ylsulfanyl]-butyric acid methyl ester (75111-35-2,80184-98-1,80225-28-1,84893-57-2,84893-58-3)

Guidance literature:

Multi-step reaction with 14 steps

1: NH₃ / 36 h / 130 °C

2: CrO₃/H₂SO₄ / H₂O; acetone / -20 °C

3: ClSi(CH₃)3, pyridine / CH₂Cl₂ / Heating

4: Raney-Ni / 2-methyl-propan-2-ol / Ambient temperature

5: H₂ / Pd-C / methanol / 25 °C

6: pyridine / 5 °C

7: p-TsOH / methanol / 25 °C

8: DMSO, oxalylchloride / CH₂Cl₂ / -60 °C

9: NaH / 1,2-dimethoxy-ethane / 25 °C

10: ZnBH₄ / 1,2-dimethoxy-ethane / 25 °C

11: pyridine / 5 °C

12: P₄S₁₀*pyridine / pyridine / 80 °C

13: NaH / 1,2-dimethoxy-ethane / 25 °C

14: K₂CO₃ / methanol / 25 °C

With pyridine; chromium(VI) oxide; chloro-trimethyl-silane; zinc(II) tetrahydroborate; Chloro-oxo-acetic acid; P₂S₅-pyridine; sulfuric acid; ammonia; hydrogen; nickel; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; palladium on activated charcoal; In pyridine; methanol; 1,2-dimethoxyethane; dichloromethane; water; acetone; tert-butyl alcohol;

Reference yield:

2-[(1R,3R,5S)-3-Benzyloxy-5-hydroxy-2-(tetrahydro-pyran-2-yloxymethyl)-cyclopentyl]-acetamide (75111-19-2,80184-31-2) → 4-[(3aR,5R,6aS)-5-Hydroxy-4-((E)-3-hydroxy-oct-1-enyl)-3,3a,4,5,6,6a-hexahydro-cyclopenta[b]pyrrol-2-ylsulfanyl]-butyric acid methyl ester (75111-35-2,80184-98-1,80225-28-1,84893-57-2,84893-58-3)

Guidance literature:

Multi-step reaction with 13 steps

1: CrO₃/H₂SO₄ / H₂O; acetone / -20 °C

2: ClSi(CH₃)3, pyridine / CH₂Cl₂ / Heating

3: Raney-Ni / 2-methyl-propan-2-ol / Ambient temperature

4: H₂ / Pd-C / methanol / 25 °C

5: pyridine / 5 °C

6: p-TsOH / methanol / 25 °C

7: DMSO, oxalylchloride / CH₂Cl₂ / -60 °C

8: NaH / 1,2-dimethoxy-ethane / 25 °C

9: ZnBH₄ / 1,2-dimethoxy-ethane / 25 °C

10: pyridine / 5 °C

11: P₄S₁₀*pyridine / pyridine / 80 °C

12: NaH / 1,2-dimethoxy-ethane / 25 °C

13: K₂CO₃ / methanol / 25 °C

With pyridine; chromium(VI) oxide; chloro-trimethyl-silane; zinc(II) tetrahydroborate; Chloro-oxo-acetic acid; P₂S₅-pyridine; sulfuric acid; hydrogen; nickel; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; palladium on activated charcoal; In pyridine; methanol; 1,2-dimethoxyethane; dichloromethane; water; acetone; tert-butyl alcohol;

upstream raw materials:

Methyl 4-bromobutyrate

Acetic acid (3aS,5S,6aR)-4-((E)-3-acetoxy-oct-1-enyl)-1-thioxo-octahydro-cyclopenta[c]pyrrol-5-yl ester

Acetic acid (1R,3R,5S)-2-((E)-3-acetoxy-oct-1-enyl)-6-oxo-bicyclo[3.2.0]hept-3-yl ester

C₁₂H₁₆O₅

Refernces

• 1、 Bartmann,Beck,Knolle,Rupp. "New analogs of epoprostenol (prostacyclin)". . p. 850 - 855. Retrieved 2007/10/02.