(15S)-Latanoprost Acid

Base Information

• Chemical Name: (15S)-Latanoprost Acid
• CAS No.: 41639-84-3
• Molecular Formula: C23H34O5
• Molecular Weight: 390.52
• DSSTox Substance ID: DTXSID20471556
• Wikidata: Q82300093
• Mol file: 41639-84-3.mol

Synonyms:(15S)-Latanoprost Acid;41639-84-3;15-epi-Latanoprost Acid;(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoic acid;SCHEMBL18651274;DTXSID20471556;(Z)-7-((1R,2R,3R,5S)-3,5-Dihydroxy-2-((S)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoic acid;(Z)-7-((1R,2R,3R,5S)-3,5-Dihydroxy-2-((S)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoicacid

Chemical Property of (15S)-Latanoprost Acid

Chemical Property:

• Boiling Point: 609.1±50.0 °C(Predicted)
• PKA: 4.76±0.10(Predicted)
• PSA: 97.99000
• Density: 1.159±0.06 g/cm3(Predicted)
• LogP: 3.31940
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 390.24062418
• Heavy Atom Count: 28
• Complexity: 472

Purity/Quality:

98% ^*data from raw suppliers

(15S)-LatanoprostAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C1O)CC=CCCCC(=O)O)CCC(CCC2=CC=CC=C2)O)O
• Isomeric SMILES: C1[C@H]([C@@H]([C@H]([C@H]1O)C/C=C\CCCC(=O)O)CC[C@@H](CCC2=CC=CC=C2)O)O
• Uses: The 15-epimer of Latanoprost Acid (L177310).

Technology Process of (15S)-Latanoprost Acid

There total 9 articles about (15S)-Latanoprost 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:

(1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentenyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one (41639-73-0) → (15S)-13,14-dihydro-17-phenyl-18,19,20-trinor-PGF2α (41639-84-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / H₂, 1 M NaOH / 10percent Pd/C / ethanol / 6 h

2: 83.6 percent / K₂CO₃ / methanol / 6 h / Ambient temperature

3: 83 percent / diisobutylaluminium hydride (DIBAL) / toluene; tetrahydrofuran / 1 h / -80 - -72 °C

4: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, -15 to -10 deg C, 4 h

With sodium hydroxide; potassium tert-butylate; hydrogen; diisobutylaluminium hydride; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; toluene;

DOI:10.1021/jm00054a008

Reference yield:

(-)-Corey lactone 5-(4-phenylbenzoate) (31752-99-5) → (15S)-13,14-dihydro-17-phenyl-18,19,20-trinor-PGF2α (41639-84-3)

Guidance literature:

Multi-step reaction with 7 steps

1: DCC, phosphoric acid / 1,2-dimethoxy-ethane / a) 18 deg C, 30 min, b) RT, 2 h

2: 1.) NaH / 1.) DME, RT, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, 2 h

3: 33.1 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C

4: 65 percent / H₂, 1 M NaOH / 10percent Pd/C / ethanol / 6 h

5: 83.6 percent / K₂CO₃ / methanol / 6 h / Ambient temperature

6: 83 percent / diisobutylaluminium hydride (DIBAL) / toluene; tetrahydrofuran / 1 h / -80 - -72 °C

7: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, -15 to -10 deg C, 4 h

With sodium hydroxide; phosphoric acid; potassium tert-butylate; hydrogen; L-Selectride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; toluene;

DOI:10.1021/jm00054a008

Reference yield:

benzyl bromide (100-39-0) → (15S)-13,14-dihydro-17-phenyl-18,19,20-trinor-PGF2α (41639-84-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) NaH, 2.) n-BuLi

2: 1.) NaH / 1.) DME, RT, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, 2 h

3: 33.1 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C

4: 65 percent / H₂, 1 M NaOH / 10percent Pd/C / ethanol / 6 h

5: 83.6 percent / K₂CO₃ / methanol / 6 h / Ambient temperature

6: 83 percent / diisobutylaluminium hydride (DIBAL) / toluene; tetrahydrofuran / 1 h / -80 - -72 °C

7: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, -15 to -10 deg C, 4 h

With sodium hydroxide; n-butyllithium; potassium tert-butylate; hydrogen; L-Selectride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; toluene;

DOI:10.1021/jm00054a008

upstream raw materials:

(4-carboxybutyl)triphenylphosphonium bromide

(1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-ol

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

benzyl bromide

Downstream raw materials:

isopropyl (Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(S)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate

Refernces