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CAS No.: | 130209-76-6 |
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Name: | 17-PHENYL TRINOR PGF2ALPHA-IPR |
Article Data: | 4 |
Molecular Structure: | |
Formula: | C26H38 O5 |
Molecular Weight: | 430.585 |
Synonyms: | 5-Heptenoicacid, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-,1-methylethyl ester, (5Z)- (9CI); 5-Heptenoic acid,7-[3,5-dihydroxy-2-(3-hydroxy-5-phenyl-1-pentenyl)cyclopentyl]-, 1-methylethylester, [1R-[1a(Z),2b(1E,3S*),3a,5a]]-; 17-Phenyl-18,19,20-trinor-PGF2a-1-isopropyl ester; PhDH 100A |
Density: | 1.141g/cm3 |
Boiling Point: | 573.4°Cat760mmHg |
Flash Point: | 185°C |
PSA: | 86.99000 |
LogP: | 3.96240 |
2-iodo-propane
(5Z)-bimatoprost acid
15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone for 10h; Ambient temperature; | 80% |
15-keto-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
A
15β-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
B
15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
Conditions | Yield |
---|---|
With sodium tetrahydroborate; cerium(III) chloride In methanol; dichloromethane for 0.5h; | A 41% B 28% |
With sodium tetrahydroborate; cerium(III) chloride 1.) MeOH, CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given; |
dimethyl(2-oxo-4-phenylbutyl)phosphonate
15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) PhB(OH)2, molecular sieves 3A, 2.) PCC, AlCl3, 3.) DIPEA, LiCl, 4.) aq. H2O2 2: 1.) CeCl3*7H2O, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C, 1 h View Scheme |
(Z)-7-((1R,2S,3R,5S)-3,5-Dihydroxy-2-hydroxymethyl-cyclopentyl)-hept-5-enoic acid isopropyl ester
15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) PhB(OH)2, molecular sieves 3A, 2.) PCC, AlCl3, 3.) DIPEA, LiCl, 4.) aq. H2O2 2: 1.) CeCl3*7H2O, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C, 1 h View Scheme |
15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: NaHSO4*H2O / tetrahydrofuran; H2O / 13 h / Ambient temperature 2: 1.) PhB(OH)2, molecular sieves 3A, 2.) PCC, AlCl3, 3.) DIPEA, LiCl, 4.) aq. H2O2 3: 1.) CeCl3*7H2O, 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C, 30 min, 2.) -78 deg C, 1 h View Scheme |
Isopropyl (Z)-7-((1R,2R,3R,5S)-2-((3S,E)-3-(tert-butyldimethylsilyloxy)-5-phenyl-pent-1-enyl)-3-(tert-butyldimethylsilyloxy)-5-hydroxy-cyclopentyl)-hept-5-enoate
15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
Conditions | Yield |
---|---|
With hydrogen fluoride In water; isopropyl alcohol Product distribution / selectivity; |
isobutylamine
15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
17-phenyl-trinor-prostaglandin F2α isobutylamide
Conditions | Yield |
---|---|
In methanol at 80℃; for 24 - 48h; | 80% |
15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
15-keto-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane for 24h; Ambient temperature; | 76% |
propylamine
15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
bimatoprost
Conditions | Yield |
---|---|
In methanol at 90℃; | 62% |
15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
A
(Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2S,3S)-3-((S)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester
B
(Z)-7-{(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(2R,3R)-3-((S)-1-hydroxy-3-phenyl-propyl)-oxiranyl]-cyclopentyl}-hept-5-enoic acid isopropyl ester
Conditions | Yield |
---|---|
With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; dihydrogen peroxide; phenylboronic acid Product distribution; multistep reaction; stereoselective epoxidation of 17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester and its 15-R epimer; regio- and stereoselective reactions of epoxides formed; | |
With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; dihydrogen peroxide; phenylboronic acid Yield given. Multistep reaction. Yields of byproduct given; | |
With titanium(IV) isopropylate; tert.-butylhydroperoxide; (-)-diisopropyl tartrate; dihydrogen peroxide; phenylboronic acid Yield given. Multistep reaction. Yields of byproduct given; |