5-[(1R,2R,3S,5R,6R,7R)-6-((E)-(S)-3-Hydroxy-7-phenyl-hept-1-enyl)-2-iodo-9-oxa-tricyclo[3.3.1.0^3,7]non-1-yl]-pentanoic acid methyl ester

Base Information

• Chemical Name: 5-[(1R,2R,3S,5R,6R,7R)-6-((E)-(S)-3-Hydroxy-7-phenyl-hept-1-enyl)-2-iodo-9-oxa-tricyclo[3.3.1.0^3,7]non-1-yl]-pentanoic acid methyl ester
• CAS No.: 141887-84-5
• Molecular Formula: C₂₇H₃₇IO₄
• Molecular Weight: 552.493

Synonyms:5-[(1R,2R,3S,5R,6R,7R)-6-((E)-(S)-3-Hydroxy-7-phenyl-hept-1-enyl)-2-iodo-9-oxa-tricyclo[3.3.1.0^3,7]non-1-yl]-pentanoic acid methyl ester

Chemical Property of 5-[(1R,2R,3S,5R,6R,7R)-6-((E)-(S)-3-Hydroxy-7-phenyl-hept-1-enyl)-2-iodo-9-oxa-tricyclo[3.3.1.0^3,7]non-1-yl]-pentanoic acid methyl ester

Chemical Property:

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Technology Process of 5-[(1R,2R,3S,5R,6R,7R)-6-((E)-(S)-3-Hydroxy-7-phenyl-hept-1-enyl)-2-iodo-9-oxa-tricyclo[3.3.1.0^3,7]non-1-yl]-pentanoic acid methyl ester

There total 15 articles about 5-[(1R,2R,3S,5R,6R,7R)-6-((E)-(S)-3-Hydroxy-7-phenyl-hept-1-enyl)-2-iodo-9-oxa-tricyclo[3.3.1.0^3,7]non-1-yl]-pentanoic 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: 77.0%

5-[(3aS,5R,6R,6aS)-5-Hydroxy-6-((E)-(S)-3-hydroxy-7-phenyl-hept-1-enyl)-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl]-pentanoic acid methyl ester (141887-83-4) → 5-[(1R,2R,3S,5R,6R,7R)-6-((E)-(S)-3-Hydroxy-7-phenyl-hept-1-enyl)-2-iodo-9-oxa-tricyclo[3.3.1.03,7]non-1-yl]-pentanoic acid methyl ester (141887-84-5)

Guidance literature:

With iodine; In methanol; water; benzene; for 0.0833333h; Ambient temperature;

DOI:10.1016/S0040-4020(01)88526-4

Reference yield:

methyl (2E,4E)-5-(3-nitrophenyl)-2,4-pentadienoate (92356-69-9) → 5-[(1R,2R,3S,5R,6R,7R)-6-((E)-(S)-3-Hydroxy-7-phenyl-hept-1-enyl)-2-iodo-9-oxa-tricyclo[3.3.1.03,7]non-1-yl]-pentanoic acid methyl ester (141887-84-5)

Guidance literature:

Multi-step reaction with 10 steps

1: H₂ / 5percent Pd/C / methanol; benzene / 25 °C

2: 62 percent / pyridine / Ambient temperature

3: 1) n-BuLi / 1) THF, hexane, -78 deg C, 2) -78 deg C

4: AcOH, H₂O / tetrahydrofuran

5: 1) NaNO₂, AcOH, 2) NaN₃ / 1) THF, H₂O, 0 deg C, 2) 0 deg C

6: 1) NaH / 1) DME, toluene, oil, r.t., 2) DME, toluene

7: 38 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.05 h / 0 °C

8: 63 percent / H₂ / 5percent Pd/C / methanol / 0.17 h / Ambient temperature

9: 1) NaNO₂, AcOH, 2) H₃PO₂ / 1) H₂O, 0 deg C, 10 min, 2) H₂O, 0 deg C, 10 min

10: 77 percent / I₂ / methanol; H₂O; benzene / 0.08 h / Ambient temperature

With pyridine; sodium tetrahydroborate; n-butyllithium; sodium azide; cerium(III) chloride; water; hydrogen; iodine; hypophosphorous acid; sodium hydride; acetic acid; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; water; benzene;

DOI:10.1016/S0040-4020(01)88526-4

Reference yield:

3-nitro-benzaldehyde (99-61-6) → 5-[(1R,2R,3S,5R,6R,7R)-6-((E)-(S)-3-Hydroxy-7-phenyl-hept-1-enyl)-2-iodo-9-oxa-tricyclo[3.3.1.03,7]non-1-yl]-pentanoic acid methyl ester (141887-84-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 1) LiN3)3>2 / 1) THF, -78 deg C, 2 h, 2) THF, a) -45 deg C, 10 min, b) 23 deg C, 18 h

2: H₂ / 5percent Pd/C / methanol; benzene / 25 °C

3: 62 percent / pyridine / Ambient temperature

4: 1) n-BuLi / 1) THF, hexane, -78 deg C, 2) -78 deg C

5: AcOH, H₂O / tetrahydrofuran

6: 1) NaNO₂, AcOH, 2) NaN₃ / 1) THF, H₂O, 0 deg C, 2) 0 deg C

7: 1) NaH / 1) DME, toluene, oil, r.t., 2) DME, toluene

8: 38 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.05 h / 0 °C

9: 63 percent / H₂ / 5percent Pd/C / methanol / 0.17 h / Ambient temperature

10: 1) NaNO₂, AcOH, 2) H₃PO₂ / 1) H₂O, 0 deg C, 10 min, 2) H₂O, 0 deg C, 10 min

11: 77 percent / I₂ / methanol; H₂O; benzene / 0.08 h / Ambient temperature

With pyridine; sodium tetrahydroborate; n-butyllithium; sodium azide; cerium(III) chloride; water; hydrogen; iodine; hypophosphorous acid; sodium hydride; acetic acid; lithium hexamethyldisilazane; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; water; benzene;

DOI:10.1016/S0040-4020(01)88526-4

upstream raw materials:

5-[(3aS,5R,6R,6aS)-5-Hydroxy-6-((E)-(S)-3-hydroxy-7-phenyl-hept-1-enyl)-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl]-pentanoic acid methyl ester

methyl (2E,4E)-5-(3-nitrophenyl)-2,4-pentadienoate

3-nitro-benzaldehyde

isocarbacyclin

Downstream raw materials:

5-{(1R,2R,3S,5R,6R,7R)-2-Iodo-6-[(E)-(S)-7-phenyl-3-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-hept-1-enyl]-9-oxa-tricyclo[3.3.1.0^3,7]non-1-yl}-pentanoic acid methyl ester

5-[(1S,3S,4S,5R,7R)-4-((S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxymethyl)-9-oxa-tricyclo[3.3.1.0^3,7]non-1-yl]-pentanoic acid methyl ester

5-[(1R,2R,3S,5R,6S,7R)-2-Iodo-6-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxymethyl)-9-oxa-tricyclo[3.3.1.0^3,7]non-1-yl]-pentanoic acid methyl ester

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