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

Base Information

• Chemical Name: 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
• CAS No.: 141887-98-1
• Molecular Formula: C₂₅H₃₁F₃O₆
• Molecular Weight: 484.513

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

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Technology Process of 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

There total 12 articles about 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 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: 86.0%

5-[(1R,2R,3S,5R,6S,7R)-2-Iodo-6-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxymethyl)-9-oxa-tricyclo[3.3.1.03,7]non-1-yl]-pentanoic acid methyl ester (141887-97-0) → 5-[(1S,3S,4S,5R,7R)-4-((S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxymethyl)-9-oxa-tricyclo[3.3.1.03,7]non-1-yl]-pentanoic acid methyl ester (141887-98-1)

Guidance literature:

With di-tert-butyl peroxide; tri-n-butyl-tin hydride; In toluene; at 85 ℃; for 3h;

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

Reference yield:

isocarbacyclin (88931-51-5) → 5-[(1S,3S,4S,5R,7R)-4-((S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxymethyl)-9-oxa-tricyclo[3.3.1.03,7]non-1-yl]-pentanoic acid methyl ester (141887-98-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 93 percent / TBHP, L-(+)-DIPT, Ti(O-i-C₃H₇)4, molecular sieves / CH₂Cl₂; toluene / 6.5 h / -20 °C

2: 96 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 48 h / 21 °C

3: 1) AcOH, H₂O, 2) 20percent aq. K₂CO₃ / 1) 100 deg C, 100 min, 2) r.t., 1 h

4: NaIO₄ / tetrahydrofuran; diethyl ether; H₂O / 1 h / Ambient temperature

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

6: 38 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.05 h / 0 °C

7: 63 percent / H₂ / 5percent Pd/C / methanol / 0.17 h / Ambient temperature

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

9: 77 percent / I₂ / methanol; H₂O; benzene / 0.08 h / Ambient temperature

10: 95 percent / pyridine / CH₂Cl₂ / 3.5 h / 20 °C

12: 86 percent / Bu₃SnH, (tBuO)2 / toluene / 3 h / 85 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; sodium periodate; molecular sieve; cerium(III) chloride; L-(+)-diisopropyl tartrate; di-tert-butyl peroxide; water; hydrogen; iodine; tri-n-butyl-tin hydride; hypophosphorous acid; sodium hydride; potassium carbonate; acetic acid; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; benzene;

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

Reference yield:

methyl (1R,5S,6S,7R)-6-formyl-7-hydroxybicyclo<3.3.0>oct-2-ene-3-pentanoate (140900-71-6) → 5-[(1S,3S,4S,5R,7R)-4-((S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxymethyl)-9-oxa-tricyclo[3.3.1.03,7]non-1-yl]-pentanoic acid methyl ester (141887-98-1)

Guidance literature:

Multi-step reaction with 8 steps

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

2: 38 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 0.05 h / 0 °C

3: 63 percent / H₂ / 5percent Pd/C / methanol / 0.17 h / Ambient temperature

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

5: 77 percent / I₂ / methanol; H₂O; benzene / 0.08 h / Ambient temperature

6: 95 percent / pyridine / CH₂Cl₂ / 3.5 h / 20 °C

8: 86 percent / Bu₃SnH, (tBuO)2 / toluene / 3 h / 85 °C

With pyridine; sodium tetrahydroborate; cerium(III) chloride; di-tert-butyl peroxide; hydrogen; iodine; tri-n-butyl-tin hydride; hypophosphorous acid; sodium hydride; acetic acid; sodium nitrite; palladium on activated charcoal; In methanol; dichloromethane; water; toluene; benzene;

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

upstream raw materials:

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

isocarbacyclin

methyl (1R,5S,6S,7R)-6-formyl-7-hydroxybicyclo<3.3.0>oct-2-ene-3-pentanoate

13,14-epoxy-13,14-dihydroisocarbacyclin methyl ester

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