Fluprostenol Lactone Diol CAS#: 53872-60-9; ChemWhat Code: 857796

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product NameFluprostenol Lactone Diol
IUPAC Name(3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one  
Molecular Structure
CAS Registry Number 53872-60-9
Synonyms(3aR,4R,5R,6aS)-5-Hydroxy-4-((R,E)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)but-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one
53872-60-9
(3Ar,4R,5R,6aS)-5-hydroxy-4-[(E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
(+)-(3aR,4R,5r,6aS)-Hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-4-(3-trifluoromethyl)phenoxy-1-butenyl]-2H-cyclopenta[b]furan-2-one
(3AR,4R,5R,6AS)-5-HYDROXY-4-((R,E)-3-HYDROXY-4-(3-(TRIFLUOROMETHYL)-PHENOXY)BUT-1-EN-1-YL)HEXAHYDRO-2H-CYCLOPENTA[B]FURAN-2-ONE
SCHEMBL1838024
HMS3649I17
AMY30073
AKOS015896619
C15945
SR-01000946575
J-501157
SR-01000946575-1
(3aR,4R,5R,6aS)-4-((R,E)-4-(3-(trifluoromethyl)phenoxy)-3-hydroxybut-1-enyl)-hexahydro-5-hydroxycyclopenta[b]furan-2-one
2H-Cyclopenta[b]furan-2-one, hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-, (3aR,4R,5R,6aS)-
Molecular FormulaC18H19F3O5
Molecular Weight372.3
InChIInChI=1S/C18H19F3O5/c19-18(20,21)10-2-1-3-12(6-10)25-9-11(22)4-5-13-14-7-17(24)26-16(14)8-15(13)23/h1-6,11,13-16,22-23H,7-9H2/b5-4+/t11-,13-,14-,15-,16+/m1/s1  
InChI KeyXYSPYIAAWRUEML-AVMWIMHJSA-N
Canonical SMILESC1[C@H]([C@@H]([C@@H]2[C@H]1OC(=O)C2)/C=C/[C@H](COC3=CC=CC(=C3)C(F)(F)F)O)O 
Patent Information
Patent IDTitlePublication Date
US2015/51410PROCESSES AND INTERMEDIATES FOR THE PREPARATIONS OF ISOMER FREE PROSTAGLANDINS2015
WO2011/55377A NOVEL PROCESS FOR THE PREPARATION OF PROSTAGLANDINS AND INTERMEDIATES THEREOF2011
US2007/167641Processes and intermediates for the preparations of prostaglandins2007
 EP1810967Processes and intermediates for the preparations of prostaglandins2007

Physical Data

No data available

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHz
Chemical shifts1Hchloroform-d1400
Fluprostenol Lactone Diol CAS#: 53872-60-9 NMR

Route of Synthesis (ROS)

Route of Synthesis (ROS) of Fluprostenol Lactone Diol CAS 53872-60-9

ConditionsYield
With toluene-4-sulfonic acid In tetrahydrofuran at 20℃; for 2.5h;87.5%
With toluene-4-sulfonic acid In tetrahydrofuran at 20℃; for 2.5h;87.5%
With toluene-4-sulfonic acid In dichloromethane for 0.5h;
With pyridinium p-toluenesulfonate In dichloromethane at 15 – 30℃;

Experimental Procedure
3,4-dihydropyran (113 gm, 5 eq) was added to a solution of DCM (1500ml) and compound (VI) (100 gm, 1 eq) at 15-20°C. PPTS (6.75 gm, 0.1 eq) was added and reaction mixture was stirred for 4-6 hrs at 20°C to 30°C. After completion of the reaction, 5%NaHCC>3 solution (1 lit) was added to the reaction mass and stirred for 10-15 min. Organic layer was washed with DM water and 10% NaCl solution (500ml). Organic layer was distilled off under vacuum to afford compound (VII) as colourless oil. Yield: 137 gm, 95% HPLC: D 94%

Safety and Hazards

Pictogram(s)exclamation-markhealth-hazard
SignalWarning
GHS Hazard StatementsH315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H361 (50%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
H362 (50%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]
Precautionary Statement CodesP203, P260, P261, P263, P264, P264+P265, P270, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)

Other Data

TransportationUnder room temperature away from light
Under room temperature away from light
HS Code
StorageUnder room temperature away from light
Shelf Life1 year
Market Price
Druglikeness
Lipinski rules component
Molecular Weight372.341
logP2.28
HBA4
HBD2
Matching Lipinski Rules4
Veber rules component
Polar Surface Area (PSA)75.99
Rotatable Bond (RotB)6
Matching Veber Rules2
Use Pattern
Fluprostenol Lactone Diol CAS#: 53872-60-9 is usually used as a Travoprost intermediate.

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