(Z)-7-{(1R,2R,3R,5S)-2-[(E)-(S)-5-(4-Azido-3-iodo-phenyl)-3-hydroxy-pent-1-enyl]-3,5-dihydroxy-cyclopentyl}-hept-5-enoic acid methyl ester

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Chemical Name:(Z)-7-{(1R,2R,3R,5S)-2-[(E)-(S)-5-(4-Azido-3-iodo-phenyl)-3-hydroxy-pent-1-enyl]-3,5-dihydroxy-cyclopentyl}-hept-5-enoic acid methyl ester
CAS No.:117625-35-1
Molecular Formula:C₂₄H₃₂IN₃O₅
Molecular Weight:569.44
Hs Code.:

Synonyms:(Z)-7-{(1R,2R,3R,5S)-2-[(E)-(S)-5-(4-Azido-3-iodo-phenyl)-3-hydroxy-pent-1-enyl]-3,5-dihydroxy-cyclopentyl}-hept-5-enoic acid methyl ester

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Chemical Property of (Z)-7-{(1R,2R,3R,5S)-2-[(E)-(S)-5-(4-Azido-3-iodo-phenyl)-3-hydroxy-pent-1-enyl]-3,5-dihydroxy-cyclopentyl}-hept-5-enoic acid methyl ester

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Technology Process of (Z)-7-{(1R,2R,3R,5S)-2-[(E)-(S)-5-(4-Azido-3-iodo-phenyl)-3-hydroxy-pent-1-enyl]-3,5-dihydroxy-cyclopentyl}-hept-5-enoic acid methyl ester

There total 16 articles about (Z)-7-{(1R,2R,3R,5S)-2-[(E)-(S)-5-(4-Azido-3-iodo-phenyl)-3-hydroxy-pent-1-enyl]-3,5-dihydroxy-cyclopentyl}-hept-5-enoic acid methyl ester 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: 93.0%

: 117625-34-0
(15S)-17-(4-azido-3-iodophenyl)-18,19,20-trinorprostaglandin F_2α methyl ester 9,11,15-tris(tert-butyldimethylsilyl ether)

: 117625-35-1
(Z)-7-{(1R,2R,3R,5S)-2-[(E)-(S)-5-(4-Azido-3-iodo-phenyl)-3-hydroxy-pent-1-enyl]-3,5-dihydroxy-cyclopentyl}-hept-5-enoic acid methyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 14h;
DOI:10.1021/jm00121a046

Reference yield:

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

: 117625-35-1
(Z)-7-{(1R,2R,3R,5S)-2-[(E)-(S)-5-(4-Azido-3-iodo-phenyl)-3-hydroxy-pent-1-enyl]-3,5-dihydroxy-cyclopentyl}-hept-5-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 12 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

10: 1) NaI, chloramine-T hydrate, 2) Zn / 1) glacial acetic acid, 25 deg C, 2 min, 2) glacial acetic acid, 25 deg C, 2.5 h

12: 93 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 14 h / 25 °C

With 1H-imidazole; methanol; sodium tetrahydroborate; cerium(III) chloride; 2,2'-bipyridine-chromium(VI) oxide; Celite; tetrabutyl ammonium fluoride; chloroamine-T; sodium hydride; diisobutylaluminium hydride; potassium carbonate; sodium iodide; zinc; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm00121a046

Reference yield:

: 35418-07-6
methyl 3-(4-aminophenyl)propionate

: 117625-35-1
(Z)-7-{(1R,2R,3R,5S)-2-[(E)-(S)-5-(4-Azido-3-iodo-phenyl)-3-hydroxy-pent-1-enyl]-3,5-dihydroxy-cyclopentyl}-hept-5-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 13 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

11: 1) NaI, chloramine-T hydrate, 2) Zn / 1) glacial acetic acid, 25 deg C, 2 min, 2) glacial acetic acid, 25 deg C, 2.5 h

13: 93 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 14 h / 25 °C

With pyridine; 1H-imidazole; methanol; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; tetrabutyl ammonium fluoride; chloroamine-T; sodium hydride; diisobutylaluminium hydride; potassium carbonate; sodium iodide; zinc; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm00121a046