Product Name

  • Name

    Latanoprost acid

  • EINECS
  • CAS No. 41639-83-2
  • Article Data22
  • CAS DataBase
  • Density 1.16 g/cm3
  • Solubility DMSO: freely soluble
  • Melting Point
  • Formula C23H34O5
  • Boiling Point 609.1 °C at 760 mmHg
  • Molecular Weight 390.52
  • Flash Point 336.2 °C
  • Transport Information
  • Appearance Pale yellow oil
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 41639-83-2 (Latanoprost acid)
  • Hazard Symbols
  • Synonyms 5-Heptenoicacid, 7-[3,5-dihydroxy-2-(3-hydroxy-5-phenylpentyl)cyclopentyl]-, [1R-[1a(Z),2b(R*),3a,5a]]-;13,14-Dihydro-17-phenyl-18,19,20-trinor-PGF2a;PhXA 85;
  • PSA 97.99000
  • LogP 3.31940

Synthetic route

(Z)-3-hydroxy-2-(hydroxymethyl)-2-methylpropyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate
913258-32-9

(Z)-3-hydroxy-2-(hydroxymethyl)-2-methylpropyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
With lithium hydroxide In methanol; water for 8h;99%
Stage #1: (Z)-3-hydroxy-2-(hydroxymethyl)-2-methylpropyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate With lithium hydroxide In methanol; water at 20℃; for 5.5 - 8h;
Stage #2: With sodium hydrogen sulfate; ammonium chloride In methanol; water; ethyl acetate Product distribution / selectivity;		99%
(Z)-methyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate
913258-31-8

(Z)-methyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
With lithium hydroxide In methanol; water at 20℃; for 20h;96%
Stage #1: methyl (Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate With lithium hydroxide In methanol; water at 20℃; for 20h;
Stage #2: With sodium hydrogen sulfate; ammonium chloride In methanol; water; ethyl acetate		96%
(Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoic acid
1240483-23-1

(Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoic acid

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
Stage #1: (Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoic acid With hydrogenchloride; water In tetrahydrofuran at 20℃; for 18h;
Stage #2: In tetrahydrofuran pH=6.8; Aqueous phosphate buffer;		91%
Stage #1: (Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoic acid With hydrogenchloride In tetrahydrofuran; water at 20℃; for 18h;
Stage #2: In tetrahydrofuran; water pH=6.8; Aqueous phosphate buffer;		91%
latanoprost
130209-82-4

latanoprost

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
Stage #1: latanoprost With lithium hydroxide; water In tetrahydrofuran for 16h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water		90%
(3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol

(3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
With hydrogenchloride; water In tetrahydrofuran at 20℃; for 17h;87%
With hydrogenchloride In methanol; water for 3.33333h;
(8aR,9R,10R,14aS,Z)-10-hydroxy-9-((3R)-3-hydroxy-5-phenylpentyl)-4,5,8,8a,9,10,11,11a-octahydrocyclopenta[b]oxecin-2(3H)-one

(8aR,9R,10R,14aS,Z)-10-hydroxy-9-((3R)-3-hydroxy-5-phenylpentyl)-4,5,8,8a,9,10,11,11a-octahydrocyclopenta[b]oxecin-2(3H)-one

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
With water; potassium hydroxide In water; isopropyl alcohol at 50℃; for 2h; Reagent/catalyst; Temperature;68%
With potassium hydroxide In water; isopropyl alcohol at 50℃; for 2h;
(4-carboxybutyl)triphenylphosphonium bromide
17814-85-6

(4-carboxybutyl)triphenylphosphonium bromide

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

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

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
With potassium tert-butylate 1.) THF, RT, 30 min, 2.) THF, -15 to -10 deg C, 4 h; Multistep reaction;
(S)-4-phenyl-1-iodo-2-(triethylsiloxy)butane
913258-20-5

(S)-4-phenyl-1-iodo-2-(triethylsiloxy)butane

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 99 percent / LiOH*H2O / methanol; H2O / 8 h
View Scheme
(S)-4-phenyl-1-(p-tolylsulfonyloxy)-2-(triethylsiloxy)butane
913258-19-2

(S)-4-phenyl-1-(p-tolylsulfonyloxy)-2-(triethylsiloxy)butane

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 89 percent / NaI; pyridine / dimethylformamide / 2.5 h / 75 - 80 °C
2: 99 percent / LiOH*H2O / methanol; H2O / 8 h
View Scheme
methyl (Z)-7-[(1R,2R,3R,5S)-2-((3S)-3-triethylsilyloxy-5-phenyl-1-(phenylsulfonyl)pentyl)-3,5-bis(triethylsilyloxy)cyclopentyl]hept-5-enoate
930118-48-2

methyl (Z)-7-[(1R,2R,3R,5S)-2-((3S)-3-triethylsilyloxy-5-phenyl-1-(phenylsulfonyl)pentyl)-3,5-bis(triethylsilyloxy)cyclopentyl]hept-5-enoate

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 45 mg / PPTS / acetone; H2O / 6 h / 20 °C
2: 96 percent / LiOH*H2O / methanol; H2O / 20 h / 20 °C
View Scheme
1-{(Z)-6-[(1R,2R,3R,5S)-2-[(R)-3-(triethylsilyloxy)-5-phenylpentyl]-3,5-bis(triethylsilyloxy)cyclopentyl]hex-4-enyl}-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane
913258-28-3

1-{(Z)-6-[(1R,2R,3R,5S)-2-[(R)-3-(triethylsilyloxy)-5-phenylpentyl]-3,5-bis(triethylsilyloxy)cyclopentyl]hex-4-enyl}-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / PPTS / acetone; H2O / 5 h / 18 °C
2: 99 percent / LiOH*H2O / methanol; H2O / 8 h
View Scheme
1-{(Z)-6-[(1R,2R,3R,5S)-2-[(3S)-3-(triethylsilyloxy)-5-phenyl-1-(phenylsulfonyl)pentyl]-3,5-bis(triethylsilyloxy)cyclopentyl]hex-4-enyl}-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane

1-{(Z)-6-[(1R,2R,3R,5S)-2-[(3S)-3-(triethylsilyloxy)-5-phenyl-1-(phenylsulfonyl)pentyl]-3,5-bis(triethylsilyloxy)cyclopentyl]hex-4-enyl}-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 99 percent / Na2HPO4; Na/Hg / methanol / 0 - 20 °C
2: 95 percent / PPTS / acetone; H2O / 5 h / 18 °C
3: 99 percent / LiOH*H2O / methanol; H2O / 8 h
View Scheme
2,2-bis(hydroxymethyl)propyl-(Z)-7-[(1R,2R,3R,5S)-2-[(3S)-3-triethylsilyloxy-5-phenyl-1-(phenylsulfonyl)pentyl]-3,5-bis(triethylsilyloxy)cyclopentyl]hept-5-enoate
913258-25-0

2,2-bis(hydroxymethyl)propyl-(Z)-7-[(1R,2R,3R,5S)-2-[(3S)-3-triethylsilyloxy-5-phenyl-1-(phenylsulfonyl)pentyl]-3,5-bis(triethylsilyloxy)cyclopentyl]hept-5-enoate

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 227 mg / Na2HPO4; Na/Hg / methanol / 2 h
2: 45 mg / PPTS / acetone; H2O / 6 h / 20 °C
3: 96 percent / LiOH*H2O / methanol; H2O / 20 h / 20 °C
View Scheme
4-Phenyl-1-butene
768-56-9

4-Phenyl-1-butene

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: (K3Fe(CN)6; K2OsO2(OH)4; K2CO3 / (DHQ)2AQN / 2-methyl-propan-2-ol; H2O / 17 h / 0 °C
2: 67.4 percent / Bu2SnO; Et3N / CH2Cl2 / 0 - 20 °C
3: 99.5 percent / imidazole; Et3N / dimethylformamide / 1.33 h / 0 - 20 °C
4: 89 percent / NaI; pyridine / dimethylformamide / 2.5 h / 75 - 80 °C
5: 99 percent / LiOH*H2O / methanol; H2O / 8 h
View Scheme
Multi-step reaction with 10 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 25.5 h / 0 - 20 °C
2.1: [(S,S)-N,N’-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(II); acetic acid / tetrahydrofuran; water / 24 h / 0 - 20 °C
3.1: n-butyllithium / tetrahydrofuran / -20 °C
3.2: -20 - 20 °C
4.1: 1H-imidazole / dichloromethane / 16 h / 0 - 20 °C
5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere
5.2: 2 h / 20 °C / Inert atmosphere
6.1: iodine; triphenylphosphine; 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere
7.1: tert.-butyl lithium / diethyl ether / 4 h / -78 - -40 °C / Inert atmosphere
7.2: 1 h / -78 - -20 °C / Inert atmosphere
8.1: ozone / methanol; dichloromethane / -78 °C
8.2: 3.25 h / -78 - 20 °C / Inert atmosphere
9.1: hydrogenchloride; water / tetrahydrofuran / 16 h / 20 °C
10.1: potassium tert-butylate / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere
10.2: 1.5 h / 0 - 20 °C / Inert atmosphere
View Scheme
benzyltriphenylphosphonium bromide
1449-46-3

benzyltriphenylphosphonium bromide

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: hexyllithium / tetrahydrofuran; hexane / 1.5 h / 5 - 15 °C
1.2: 62 percent / tetrahydrofuran; hexane / 2 h / 20 °C
2.1: 98.8 percent / H2 / Pd/C / methanol / 24 h / 30 °C / 7500.6 Torr
3.1: 99 percent / PTSA / methanol / 4 h / 40 °C
4.1: 67.4 percent / Bu2SnO; Et3N / CH2Cl2 / 0 - 20 °C
5.1: 99.5 percent / imidazole; Et3N / dimethylformamide / 1.33 h / 0 - 20 °C
6.1: 89 percent / NaI; pyridine / dimethylformamide / 2.5 h / 75 - 80 °C
7.1: 99 percent / LiOH*H2O / methanol; H2O / 8 h
View Scheme
(S)-4-phenyl-1,2-butanediol
124988-64-3

(S)-4-phenyl-1,2-butanediol

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 67.4 percent / Bu2SnO; Et3N / CH2Cl2 / 0 - 20 °C
2: 99.5 percent / imidazole; Et3N / dimethylformamide / 1.33 h / 0 - 20 °C
3: 89 percent / NaI; pyridine / dimethylformamide / 2.5 h / 75 - 80 °C
4: 99 percent / LiOH*H2O / methanol; H2O / 8 h
View Scheme
(S)-2-hydroxy-4-phenylbutyl 4-methylbenzenesulfonate
118629-73-5

(S)-2-hydroxy-4-phenylbutyl 4-methylbenzenesulfonate

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 99.5 percent / imidazole; Et3N / dimethylformamide / 1.33 h / 0 - 20 °C
2: 89 percent / NaI; pyridine / dimethylformamide / 2.5 h / 75 - 80 °C
3: 99 percent / LiOH*H2O / methanol; H2O / 8 h
View Scheme
(4S)-2,2-dimethyl-4-styryl-1,3-dioxolane
152203-65-1

(4S)-2,2-dimethyl-4-styryl-1,3-dioxolane

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 98.8 percent / H2 / Pd/C / methanol / 24 h / 30 °C / 7500.6 Torr
2: 99 percent / PTSA / methanol / 4 h / 40 °C
3: 67.4 percent / Bu2SnO; Et3N / CH2Cl2 / 0 - 20 °C
4: 99.5 percent / imidazole; Et3N / dimethylformamide / 1.33 h / 0 - 20 °C
5: 89 percent / NaI; pyridine / dimethylformamide / 2.5 h / 75 - 80 °C
6: 99 percent / LiOH*H2O / methanol; H2O / 8 h
View Scheme
(4S)-2,2-dimethyl-4-(2-phenylethyl)-1,3-dioxolane
157732-87-1

(4S)-2,2-dimethyl-4-(2-phenylethyl)-1,3-dioxolane

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 99 percent / PTSA / methanol / 4 h / 40 °C
2: 67.4 percent / Bu2SnO; Et3N / CH2Cl2 / 0 - 20 °C
3: 99.5 percent / imidazole; Et3N / dimethylformamide / 1.33 h / 0 - 20 °C
4: 89 percent / NaI; pyridine / dimethylformamide / 2.5 h / 75 - 80 °C
5: 99 percent / LiOH*H2O / methanol; H2O / 8 h
View Scheme
(-)-Corey lactone 5-(4-phenylbenzoate)
31752-99-5

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

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
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: 52 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C
4: 78.4 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h
5: 85 percent / K2CO3 / methanol / 6 h / Ambient temperature
6: 65 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
View Scheme
benzyl bromide
100-39-0

benzyl bromide

alcoholic potash

alcoholic potash

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
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: 52 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C
4: 78.4 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h
5: 85 percent / K2CO3 / methanol / 6 h / Ambient temperature
6: 65 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
View Scheme
(1S,5R,6R,7R)-6-(3-oxo-5-phenyl-1E-pentenyl)-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one
41639-72-9

(1S,5R,6R,7R)-6-(3-oxo-5-phenyl-1E-pentenyl)-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 52 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C
2: 78.4 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h
3: 85 percent / K2CO3 / methanol / 6 h / Ambient temperature
4: 65 percent / diisobutylaluminium hydride (DIBAL) / toluene; tetrahydrofuran / 1 h / -80 - -72 °C
5: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, -15 to -10 deg C, 4 h
View Scheme
(1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentenyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one
41639-23-0

(1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentenyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 78.4 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h
2: 85 percent / K2CO3 / methanol / 6 h / Ambient temperature
3: 65 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
View Scheme
dimethyl (2-oxo-4-phenylbutyl)phosphonate

dimethyl (2-oxo-4-phenylbutyl)phosphonate

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) NaH / 1.) DME, RT, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, 2 h
2: 52 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C
3: 78.4 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h
4: 85 percent / K2CO3 / methanol / 6 h / Ambient temperature
5: 65 percent / diisobutylaluminium hydride (DIBAL) / toluene; tetrahydrofuran / 1 h / -80 - -72 °C
6: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, -15 to -10 deg C, 4 h
View Scheme
(1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one
145773-21-3

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

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 65 percent / diisobutylaluminium hydride (DIBAL) / toluene; tetrahydrofuran / 1 h / -80 - -72 °C
2: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, -15 to -10 deg C, 4 h
View Scheme
(1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one
145773-20-2

(1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85 percent / K2CO3 / methanol / 6 h / Ambient temperature
2: 65 percent / diisobutylaluminium hydride (DIBAL) / toluene; tetrahydrofuran / 1 h / -80 - -72 °C
3: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, -15 to -10 deg C, 4 h
View Scheme
(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate
38754-71-1

(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) NaH / 1.) DME, RT, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, 2 h
2: 52 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C
3: 78.4 percent / H2, 1 M NaOH / 10percent Pd/C / ethanol / 6 h
4: 85 percent / K2CO3 / methanol / 6 h / Ambient temperature
5: 65 percent / diisobutylaluminium hydride (DIBAL) / toluene; tetrahydrofuran / 1 h / -80 - -72 °C
6: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, -15 to -10 deg C, 4 h
View Scheme
C38H70O5Si3
943315-69-3

C38H70O5Si3

C38H70O5Si3

C38H70O5Si3

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
With hydrogenchloride; water In acetone at 0 - 25℃; pH=1 - 3;
(4-carboxybutyl)triphenylphosphonium bromide
17814-85-6

(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
352276-28-9

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

latanoprost acid
41639-83-2

latanoprost acid

Conditions
ConditionsYield
Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃;
Stage #2: (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-ol In tetrahydrofuran at -17℃; for 20h; Wittig Reaction;
Stage #3: With aminosulfonic acid In tert-butyl methyl ether; water pH=1.5 - 2.0;
Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.5 - 0.666667h; Wittig Reaction;
Stage #2: (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-ol In tetrahydrofuran at -15℃; for 4 - 5h; Wittig Reaction;
Stage #1: (4-carboxybutyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.75h; Inert atmosphere;
Stage #2: (1S,5R,6R,7R)-6-<(3S)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-ol In tetrahydrofuran at -15 - -10℃; Wittig Reaction; Inert atmosphere;
L-arginine
74-79-3

L-arginine

latanoprost acid
41639-83-2

latanoprost acid

latanoprost L-arginine salt
1224443-39-3

latanoprost L-arginine salt

Conditions
ConditionsYield
In methanol; water for 0.5h; Product distribution / selectivity;100%
In methanol; water for 0.5h; Product distribution / selectivity;
2-iodo-propane
75-30-9

2-iodo-propane

latanoprost acid
41639-83-2

latanoprost acid

A

isopropyl (E)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate

isopropyl (E)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate

B

latanoprost
130209-82-4

latanoprost

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone at 20℃; for 14h;A n/a
B 99.83%
...Expand
latanoprost acid
41639-83-2

latanoprost acid

isopropyl alcohol
67-63-0

isopropyl alcohol

latanoprost
130209-82-4

latanoprost

Conditions
ConditionsYield
With Lipase Novozym 435 at 30℃; for 18h; Enzymatic reaction;92%
Novozym 435 at 30℃; for 18h;92%
With 2-chloro-1,3-dimethyl imidazolium chloride; potassium tert-butylate; triethylamine at 0 - 70℃; for 2h;
2-iodo-propane
75-30-9

2-iodo-propane

latanoprost acid
41639-83-2

latanoprost acid

latanoprost
130209-82-4

latanoprost

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;84%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 14h;72%
With potassium carbonate In N,N-dimethyl-formamide at 50℃;68%
isobutylamine
78-81-9

isobutylamine

latanoprost acid
41639-83-2

latanoprost acid

17-phenyl-13,14-dihydro-trinor-prostaglandin F2α isobutylamide
1131798-26-9

17-phenyl-13,14-dihydro-trinor-prostaglandin F2α isobutylamide

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃;70%
desmethyl anethole trithione
18274-81-2

desmethyl anethole trithione

latanoprost acid
41639-83-2

latanoprost acid

(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoic acid 4-(3H-1,2-dithiole-3-thione-5-yl)phenyl ester
1088434-86-9

(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoic acid 4-(3H-1,2-dithiole-3-thione-5-yl)phenyl ester

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;65%
Stage #1: desmethyl anethole trithione; latanoprost acid; dmap In tetrahydrofuran at 0℃; Inert atmosphere;
Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 15h; Inert atmosphere;
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap In tetrahydrofuran at 0 - 20℃; for 15h;
2-iodo-propane
75-30-9

2-iodo-propane

latanoprost acid
41639-83-2

latanoprost acid

A

isopropyl (E)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate

isopropyl (E)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate

B

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

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

C

latanoprost
130209-82-4

latanoprost

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone at 20℃; for 5.5 - 14.2167h; Product distribution / selectivity;A n/a
B n/a
C 63.2%
...Expand
5,7-Dihydroxy-3-(4-methoxy-phenyl)-chromen-4-on
491-80-5

5,7-Dihydroxy-3-(4-methoxy-phenyl)-chromen-4-on

latanoprost acid
41639-83-2

latanoprost acid

(Z)-5-hydroxy-3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate

(Z)-5-hydroxy-3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate

Conditions
ConditionsYield
In dichloromethane at 20℃;60%
2-(prop-2-yn-1-yl)pent-4-yn-1-ol
432027-96-8

2-(prop-2-yn-1-yl)pent-4-yn-1-ol

latanoprost acid
41639-83-2

latanoprost acid

(Z)-2-(prop-2-yn-1-yl)pent-4-yn-1-yl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate

(Z)-2-(prop-2-yn-1-yl)pent-4-yn-1-yl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane at 20℃; Inert atmosphere; Darkness;45%
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

latanoprost acid
41639-83-2

latanoprost acid

(Z)-7-((1R,2R,3R,5S)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-((R)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpentyl)cyclopentyl)hept-5-enoic acid

(Z)-7-((1R,2R,3R,5S)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-((R)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpentyl)cyclopentyl)hept-5-enoic acid

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h;

Latanoprost acid Specification

The Latanoprost acid, with CAS registry number 41639-83-2, has the systematic name of (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoic acid. Besides this, it is also called 5-heptenoic acid, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]-, (5Z)-. This chemical should be stored at the temperature of −20°C.

Physical properties of Latanoprost acid: (1)ACD/LogP: 2.22; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.41; (4)ACD/LogD (pH 7.4): -0.39; (5)ACD/BCF (pH 5.5): 4.42; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 59.25; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 15; (12)Polar Surface Area: 53.99 Å2; (13)Index of Refraction: 1.564; (14)Molar Refractivity: 109.55 cm3; (15)Molar Volume: 336.7 cm3; (16)Polarizability: 43.43×10-24cm3; (17)Surface Tension: 50 dyne/cm; (18)Enthalpy of Vaporization: 95.14 kJ/mol; (19)Vapour Pressure: 1.09E-15 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)CCC/C=C\C[C@H]2[C@@H](O)C[C@@H](O)[C@@H]2CC[C@@H](O)CCc1ccccc1
(2)InChI: InChI=1/C23H34O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,18-22,24-26H,2,7,10-16H2,(H,27,28)/b6-1-/t18-,19+,20+,21-,22+/m0/s1
(3)InChIKey: HNPFPERDNWXAGS-NFVOFSAMBJ
(4)Std. InChI: InChI=1S/C23H34O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,18-22,24-26H,2,7,10-16H2,(H,27,28)/b6-1-/t18-,19+,20+,21-,22+/m0/s1
(5)Std. InChIKey: HNPFPERDNWXAGS-NFVOFSAMSA-N

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