(15S)-17-<4-(tritylamino)phenyl>-18,19,20-trinorprostaglandin F_2α methyl ester 9,11,15-tris(tert-butyldimethylsilyl ether)

Base Information

• Chemical Name: (15S)-17-<4-(tritylamino)phenyl>-18,19,20-trinorprostaglandin F_2α methyl ester 9,11,15-tris(tert-butyldimethylsilyl ether)
• CAS No.: 117625-31-7
• Molecular Formula: C₆₁H₉₁NO₅Si₃
• Molecular Weight: 1002.65

Synonyms:(15S)-17-<4-(tritylamino)phenyl>-18,19,20-trinorprostaglandin F_2α methyl ester 9,11,15-tris(tert-butyldimethylsilyl ether)

Chemical Property of (15S)-17-<4-(tritylamino)phenyl>-18,19,20-trinorprostaglandin F_2α methyl ester 9,11,15-tris(tert-butyldimethylsilyl ether)

Chemical Property:

Purity/Quality:

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Technology Process of (15S)-17-<4-(tritylamino)phenyl>-18,19,20-trinorprostaglandin F_2α methyl ester 9,11,15-tris(tert-butyldimethylsilyl ether)

There total 14 articles about (15S)-17-<4-(tritylamino)phenyl>-18,19,20-trinorprostaglandin F_2α methyl ester 9,11,15-tris(tert-butyldimethylsilyl ether) 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: 91.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (15S)-17-<4-(tritylamino)phenyl>-18,19,20-trinorprostaglandin F2α methyl ester 11,15-bis(tert-butyldimethylsilyl ether) (117625-30-6) → (15S)-17-<4-(tritylamino)phenyl>-18,19,20-trinorprostaglandin F2α methyl ester 9,11,15-tris(tert-butyldimethylsilyl ether) (117625-31-7)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 25 ℃; for 4.5h;

DOI:10.1021/jm00121a046

Reference yield:

(-)-Corey lactone 5-(4-phenylbenzoate) (31752-99-5) → (15S)-17-<4-(tritylamino)phenyl>-18,19,20-trinorprostaglandin F2α methyl ester 9,11,15-tris(tert-butyldimethylsilyl ether) (117625-31-7)

Guidance literature:

Multi-step reaction with 9 steps

1: chromium trioxide-dipyridine complex, Celite / CH₂Cl₂ / 0.33 h / 0 °C

2: 1) NaH / 1) 1,2-dimethoxyethane, toluene, 25 deg C, 30 min, 2) 25 deg C, 2 h

3: 47 percent / NaBH₄, CeCl₃*7H₂O / methanol; tetrahydrofuran / 0.17 h / 25 °C

4: K₂CO₃, MeOH

5: 85 percent / imidazole / dimethylformamide / 4.5 h / 25 °C

6: DIBAL / toluene / -78 °C

9: 91 percent / imidazole / dimethylformamide / 4.5 h / 25 °C

With 1H-imidazole; methanol; sodium tetrahydroborate; cerium(III) chloride; 2,2'-bipyridine-chromium(VI) oxide; Celite; sodium hydride; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00121a046

Reference yield:

methyl 3-(4-aminophenyl)propionate (35418-07-6) → (15S)-17-<4-(tritylamino)phenyl>-18,19,20-trinorprostaglandin F2α methyl ester 9,11,15-tris(tert-butyldimethylsilyl ether) (117625-31-7)

Guidance literature:

Multi-step reaction with 10 steps

1: pyridine / 20 h / 25 °C

2: 1) n-BuLi / 1) THF, hexane, -78 deg C, 30 min, 2) toluene, THF, -78 deg C, 30 min

3: 1) NaH / 1) 1,2-dimethoxyethane, toluene, 25 deg C, 30 min, 2) 25 deg C, 2 h

4: 47 percent / NaBH₄, CeCl₃*7H₂O / methanol; tetrahydrofuran / 0.17 h / 25 °C

5: K₂CO₃, MeOH

6: 85 percent / imidazole / dimethylformamide / 4.5 h / 25 °C

7: DIBAL / toluene / -78 °C

10: 91 percent / imidazole / dimethylformamide / 4.5 h / 25 °C

With pyridine; 1H-imidazole; methanol; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; sodium hydride; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00121a046

upstream raw materials:

tert-butyldimethylsilyl chloride

(15S)-17-<4-(tritylamino)phenyl>-18,19,20-trinorprostaglandin F_2α methyl ester 11,15-bis(tert-butyldimethylsilyl ether)

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

methyl 3-(4-aminophenyl)propionate

Downstream raw materials:

(Z)-7-[(1R,2R,3R,5S)-2-[(E)-(S)-5-(4-Amino-3-iodo-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-pent-1-enyl]-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-hept-5-enoic acid methyl ester

(15S)-17-(4-azido-3-iodophenyl)-18,19,20-trinorprostaglandin F_2α

(E)-7-[(1R,2R,3R,5S)-2-[(E)-(S)-5-(4-Azido-3-iodo-phenyl)-3-(tert-butyl-dimethyl-silanyloxy)-pent-1-enyl]-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-hept-5-enoic acid methyl ester

(15S)-17-(4-azido-3-iodophenyl)-18,19,20-trinorprostaglandin F_2α methyl ester 9,11,15-tris(tert-butyldimethylsilyl ether)

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