Latanoprost supplier | CasNO.130209-82-4

Name
Latanoprost
EINECS 634-172-9
CAS No. 130209-82-4
Article Data48
CAS DataBase
Density 1.093 g/cm³
Solubility Soluble in: DMSO (25 mg/mL); ethanol (25 mg/mL)
Melting Point
Formula C₂₆H₄₀O₅
Boiling Point 583.8 °C at 760 mmHg
Molecular Weight 432.601
Flash Point 188.3 °C
Transport Information
Appearance pale yellow oil
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Lata prostaglandin;Latanoprost [USAN:BAN:INN];XA 41;Xalatan (TN);5-Heptenoic acid, 7-(3,5-dihydroxy-2-(3-hydroxy-5-phenylpentyl)cyclopentyl)-, 1-methylethyl ester, (1R-(1-alpha(Z),2-beta(R*),3-alpha,5-alpha))-;Xalatan;PhXA 41;Isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((3R)-3-hydroxy-5-phenylpentyl)cyclopentyl)-5-heptenoate;Latanoprost (JAN/USAN);
PSA 86.99000
LogP 4.18640

Synthetic route

: 75-30-9
2-iodo-propane

: 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

B: 130209-82-4
latanoprost

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone at 20℃; for 14h;	A n/a B 99.83%

...Expand

: 41639-83-2
latanoprost acid

: 67-63-0
isopropyl alcohol

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
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;

: isopropyl 11,15-bistetrahydropyranyloxy-13,14-dihydro-17-phenyl-18,19,20-trinor-PGF2α

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In methanol at 52℃; for 4h; Product distribution / selectivity;	90%
pyridinium p-toluenesulfonate In methanol at 52℃; for 4h;	90%
With pyridinium p-toluenesulfonate In dichloromethane at 40℃; Inert atmosphere;	86.1%
With toluene-4-sulfonic acid In isopropyl alcohol at 40℃; for 5h;
With ethanol; pyridinium p-toluenesulfonate at 20 - 50℃; for 3h;

: 75-30-9
2-iodo-propane

: 41639-83-2
latanoprost acid

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
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%

: 856453-33-3
C41H64O8

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In methanol at 45℃; for 6h; Product distribution / selectivity;	83.7%
pyridinium p-toluenesulfonate In methanol at 45℃; for 6h;	83.7%

: C39H46O7

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
Stage #1: C39H46O7 With hydrogen In ethyl acetate at 20℃; for 4h; Inert atmosphere; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 0℃; for 0.5h; Inert atmosphere; Stage #3: With sodium tetrahydroborate In methanol; dichloromethane; water at 0℃; for 2.5h; Inert atmosphere;	83%

: 141074-06-8
C26H38O5

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
Stage #1: C26H38O5 With 2,6-di-tert-butyl-4-methyl-phenol; diisobutylaluminium hydride In toluene at -70 - -20℃; Stage #2: With hydrogenchloride In water; toluene	75%

: 75-30-9
2-iodo-propane

: 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

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

C: 130209-82-4
latanoprost

Conditions

Conditions	Yield
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

: 75-30-9
2-iodo-propane

: C23H32O4

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
Stage #1: C23H32O4 With sodium hydride In isopropyl alcohol; mineral oil at 20 - 35℃; for 18h; Stage #2: 2-iodo-propane With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 18h;	49%

: 477884-73-4
(3aR,4R,5R,6aS)-hexahydro-5-triethylsilyoxy-4-[5-phenyl-(3R)-3-triethylsilyloxy-pentanyl]-2H-cyclopenta[β]furan-2-one

A: 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

C: 130209-82-4
latanoprost

Conditions

Conditions	Yield
Purification / work up;	A n/a B n/a C 45%

...Expand

: 31752-99-5
(-)-Corey lactone 5-(4-phenylbenzoate)

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
Multi-step reaction with 8 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 8: 38 percent / DBU / acetone / 4 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 8 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
8: 38 percent / DBU / acetone / 4 h / Ambient temperature
View Scheme

: 100-39-0
benzyl bromide

alcoholic potash: alcoholic potash

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
Multi-step reaction with 8 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 8: 38 percent / DBU / acetone / 4 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 8 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
8: 38 percent / DBU / acetone / 4 h / Ambient temperature
View Scheme

: 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

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
Multi-step reaction with 6 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 6: 38 percent / DBU / acetone / 4 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 6 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
6: 38 percent / DBU / acetone / 4 h / Ambient temperature
View Scheme

: 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

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
Multi-step reaction with 5 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 5: 38 percent / DBU / acetone / 4 h / Ambient temperature View Scheme

: dimethyl (2-oxo-4-phenylbutyl)phosphonate

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
Multi-step reaction with 7 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 7: 38 percent / DBU / acetone / 4 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 7 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
7: 38 percent / DBU / acetone / 4 h / Ambient temperature
View Scheme

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

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) t-BuOK / 1.) THF, RT, 30 min, 2.) THF, -15 to -10 deg C, 4 h 2: 38 percent / DBU / acetone / 4 h / Ambient temperature View Scheme

: 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

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
Multi-step reaction with 3 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 3: 38 percent / DBU / acetone / 4 h / Ambient temperature View Scheme

: 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

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
Multi-step reaction with 4 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 4: 38 percent / DBU / acetone / 4 h / Ambient temperature View Scheme

: 38754-71-1
(3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
Multi-step reaction with 7 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 7: 38 percent / DBU / acetone / 4 h / Ambient temperature View Scheme

Yield

: 41639-83-2
latanoprost acid

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
With caesium carbonate In water; N,N-dimethyl-formamide

: C41H76O5Si3

: C41H76O5Si3

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
With hydrogenchloride; water In acetone at 0 - 25℃; pH=1 - 3;

: 477884-76-7
C38H68O5Si2

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
With hydrogenchloride; water In tetrahydrofuran at 20℃; for 0.5h;

: 477884-76-7
C38H68O5Si2

: C38H68O5Si2

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

B: 130209-82-4
latanoprost

Conditions

Conditions	Yield
With hydrogenchloride; water In tetrahydrofuran at 20℃; for 0.5h;

...Expand

: 75-30-9
2-iodo-propane

: 1224443-39-3
latanoprost L-arginine salt

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
In methanol; water
In methanol; water

: 474944-22-4
(Z)-isopropyl 7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((R)-3-(tert-butyldimethylsilyloxy)-5-phenylpentyl)-5-hydroxycyclopentyl)hept-5-enoate

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
With hydrogenchloride; water In isopropyl alcohol at 25 - 30℃;

: 41639-83-2
latanoprost acid

: 75-26-3
isopropyl bromide

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
Stage #1: latanoprost acid With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone at 20 - 25℃; for 0.166667h; Stage #2: isopropyl bromide In acetone for 0.5h;

: 876953-73-0
tert-butyl[(1S)-3-iodo-1-phenethylpropyl]oxydimethylsilane

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: tert.-butyl lithium / hexane; diethyl ether / 4 h / -78 °C / Inert atmosphere 1.2: 0.92 h / -78 - -50 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 2.2: -50 °C 3.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C 4.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C 6.1: sodium hydride / isopropyl alcohol; mineral oil / 18 h / 20 - 35 °C 6.2: 18 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1.1: tert.-butyl lithium / diethyl ether; pentane / 4 h / -78 - -40 °C / Inert atmosphere; Schlenk technique 1.2: 0.5 h / -30 °C / Inert atmosphere; Schlenk technique 2.1: ozone / methanol; dichloromethane / -78 °C 2.2: -78 - 20 °C 3.1: hydrogenchloride; water / tetrahydrofuran / 16 h / 20 °C 4.1: potassium tert-butylate / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere; Schlenk technique 4.2: 0 - 20 °C / Inert atmosphere; Schlenk technique 5.1: caesium carbonate / N,N-dimethyl-formamide / 18 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1.1: tert.-butyl lithium / diethyl ether; pentane / 4 h / -78 - -40 °C / Inert atmosphere; Schlenk technique 1.2: 0.5 h / -30 °C / Inert atmosphere; Schlenk technique 2.1: ozone / methanol; dichloromethane / -78 °C 2.2: -78 - 20 °C 3.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C 4.1: valerianate de potassium / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique 4.2: 0 - 20 °C / Inert atmosphere; Schlenk technique 5.1: hydrogenchloride; water / tetrahydrofuran / 17 h / 20 °C 6.1: caesium carbonate / N,N-dimethyl-formamide / 18 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1.1: tert.-butyl lithium / diethyl ether / 4 h / -78 - -40 °C / Inert atmosphere 1.2: 1 h / -78 - -20 °C / Inert atmosphere 2.1: ozone / methanol; dichloromethane / -78 °C 2.2: 3.25 h / -78 - 20 °C / Inert atmosphere 3.1: hydrogenchloride; water / tetrahydrofuran / 16 h / 20 °C 4.1: potassium tert-butylate / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere 4.2: 1.5 h / 0 - 20 °C / Inert atmosphere 5.1: caesium carbonate / N,N-dimethyl-formamide / 18 h / 20 °C View Scheme

: 1261926-67-3
C31H54O3Si2

: 130209-82-4
latanoprost

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 1.2: -50 °C 2.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C 3.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C 5.1: sodium hydride / isopropyl alcohol; mineral oil / 18 h / 20 - 35 °C 5.2: 18 h / 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C
1.2: -50 °C
2.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C
3.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere
4.1: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C
5.1: sodium hydride / isopropyl alcohol; mineral oil / 18 h / 20 - 35 °C
5.2: 18 h / 20 °C
View Scheme

: 18162-48-6
tert-butyldimethylsilyl chloride

: 130209-82-4
latanoprost

: (Z)-isopropyl 7-((1R,2R,3R,5S)-3,5-bis((tert-butyldimethylsilyl)oxy)-2-((R)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpentyl)cyclopentyl)hept-5-enoate

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h;	94%

: 130209-82-4
latanoprost

: 41639-83-2
latanoprost acid

Conditions

Conditions	Yield
Stage #1: latanoprost With lithium hydroxide; water In tetrahydrofuran for 16h; Stage #2: With hydrogenchloride In tetrahydrofuran; water	90%

: 4426-47-5
butylboronic acid

: 130209-82-4
latanoprost

: (Z)-isopropyl 7-((1R,5S,6R,7R)-3-butyl-7-((R)-3-hydroxy-5-phenylpentyl)-2,4-dioxa-3-borabicyclo[3.2.1]octan-6-yl)hept-5-enoate

Conditions

Conditions	Yield
In dichloromethane at 45℃; for 20h; Inert atmosphere;	80%
In dichloromethane at 45℃; for 22h; Inert atmosphere;

: (S)-2-{(S)-2-[(S)-2-((S)-2-acetoxypropionyloxy)propionyloxy]propionyloxy}propionic acid

: 130209-82-4
latanoprost

: C68H94O32

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 28h; Inert atmosphere;	60%

: (S)-2-((S)-2-{(S)-2-[(S)-2-((S)-2-acetoxypropionyloxy)propionyloxy]propionyloxy}propionyloxy)propionic acid

: 130209-82-4
latanoprost

: propan-2-yl (5Z)-7-[3,5-bis({[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-(acetyloxy)propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy})-2-(3-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-(acetyloxy)propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}-5-phenylpentyl)cyclopentyl]hept-5-enoate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 48h; Inert atmosphere;	54%

: (2S)-2-{[(2S)-2-{[(2S)-2-(acetyloxy)propanoyl]oxy}propanoyl]oxy}propanoic acid

: 130209-82-4
latanoprost

: propan-2-yl (5Z)-7-[3,5-bis({[(2S)-2-{[(2S)-2-{[(2S)-2-(acetyloxy)propanoyl]oxy}propanoyl]oxy}propanoyl]oxy})-2-(3-{[(2S)-2-{[(2S)-2-{[(2S)-2-(acetyloxy)propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}-5-phenylpentyl)cyclopentyl]hept-5-enoate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 48h; Inert atmosphere;	37%

: (S)-2-[(S)-2-((S)-2-{(S)-2-[(S)-2-((S)-2-acetoxypropionyloxy)propionyloxy]propionyloxy}propionyloxy)propionyloxy]-propionic acid

: 130209-82-4
latanoprost

: propan-2-yl (5Z)-7-[3,5-bis({[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-(acetyloxy)propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy})-2-(3-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-{[(2S)-2-(acetyloxy)propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}propanoyl]oxy}-5-phenylpentyl)cyclopentyl]hept-5-enoate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 48h; Inert atmosphere;	35%

Latanoprost Chemical Properties

Formula: C₂₆H₄₀O₅
Mol. mass :432.593 g/mol
Other name:Latanoprost
XALATAN the brand name of Xalatan manufactured by Pfizer.It is freely soluble in DMSO.
Following is the molecular structure of XALATAN:

Latanoprost Uses

XALATAN ophthalmic solution is a topical medication used for controlling the progression of glaucoma or ocular hypertension by reducing intraocular pressure.
XALATAN is also a prostaglandin analogue that works by increasing the outflow of aqueous fluid from the eyes.

Latanoprost Toxicity Data With Reference

1.	ocu-man TDLo:33 µL/kg/25D-I:EYE	AJOPAA American Journal of Ophthalmology. 124 (1997),683.
2.	ocu-man TDLo:99 µL/kg/20W-I:SKN	AJOPAA American Journal of Ophthalmology. 124 (1997),544.
3.	ocu-wmn TDLo:4 nL/kg/5W-I:EYE	AJOPAA American Journal of Ophthalmology. 127 (1999),91.
4.	orl-rat LD50:>50 µg/kg	YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. 42 (2000),195.
5.	ivn-rat LD50:>2 mg/kg	YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. 42 (2000),195.
6.	orl-mus LD50:>50 µg/kg	YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. 42 (2000),195.
7.	ivn-mus LD50:>2 mg/kg	YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. 42 (2000),195.
8.	ivn-dog LD50:>680 µg/kg	YAKUD5 Gekkan Yakuji. Pharmaceuticals Monthly. 42 (2000),195.

RTECS : MJ9669550

Latanoprost Safety Profile

A poison by ingestion and intravenous route. Human systemic effects. When heated to decomposition it emits acrid smoke and irritating vapors.

Product Name

Latanoprost

Synthetic route

Latanoprost Chemical Properties

Latanoprost Uses

Latanoprost Toxicity Data With Reference

Latanoprost Safety Profile

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