5-{(1R,2R,3S,5R,6R,7R)-2-Iodo-6-[(E)-(S)-4-m-tolyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-but-1-enyl]-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)-2-Iodo-6-[(E)-(S)-4-m-tolyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-but-1-enyl]-9-oxa-tricyclo[3.3.1.0^3,7]non-1-yl}-pentanoic acid methyl ester
• CAS No.: 175169-69-4
• Molecular Formula: C₃₅H₄₀F₃IO₆
• Molecular Weight: 740.599

Synonyms:

Chemical Property of 5-{(1R,2R,3S,5R,6R,7R)-2-Iodo-6-[(E)-(S)-4-m-tolyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-but-1-enyl]-9-oxa-tricyclo[3.3.1.0^3,7]non-1-yl}-pentanoic acid methyl ester

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Technology Process of 5-{(1R,2R,3S,5R,6R,7R)-2-Iodo-6-[(E)-(S)-4-m-tolyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-but-1-enyl]-9-oxa-tricyclo[3.3.1.0^3,7]non-1-yl}-pentanoic acid methyl ester

There total 6 articles about 5-{(1R,2R,3S,5R,6R,7R)-2-Iodo-6-[(E)-(S)-4-m-tolyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-but-1-enyl]-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: 92.0%

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride (39637-99-5,20445-33-4) + 5-[(1R,2R,3S,5R,6R,7R)-6-((E)-(S)-3-Hydroxy-4-m-tolyl-but-1-enyl)-2-iodo-9-oxa-tricyclo[3.3.1.03,7]non-1-yl]-pentanoic acid methyl ester → 5-{(1R,2R,3S,5R,6R,7R)-2-Iodo-6-[(E)-(S)-4-m-tolyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-but-1-enyl]-9-oxa-tricyclo[3.3.1.03,7]non-1-yl}-pentanoic acid methyl ester (175169-69-4)

Guidance literature:

With pyridine;

Reference yield:

methyl 3-methylphenylacetate (53088-69-0) → 5-{(1R,2R,3S,5R,6R,7R)-2-Iodo-6-[(E)-(S)-4-m-tolyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-but-1-enyl]-9-oxa-tricyclo[3.3.1.03,7]non-1-yl}-pentanoic acid methyl ester (175169-69-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 48 percent / n-BuLi / tetrahydrofuran / -78 °C

2: 96 percent / NaH / 1,2-dimethoxy-ethane

3: 50 percent / NaBH₄, CeCl₃ / methanol

4: 89 percent / I₂ / methanol; H₂O

5: 92 percent / pyridine

With pyridine; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; iodine; sodium hydride; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; water;

Reference yield:

dimethyl [3-(3-methylphenyl)-2-oxopropane]phosphonate (61263-05-6) → 5-{(1R,2R,3S,5R,6R,7R)-2-Iodo-6-[(E)-(S)-4-m-tolyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-but-1-enyl]-9-oxa-tricyclo[3.3.1.03,7]non-1-yl}-pentanoic acid methyl ester (175169-69-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / NaH / 1,2-dimethoxy-ethane

2: 50 percent / NaBH₄, CeCl₃ / methanol

3: 89 percent / I₂ / methanol; H₂O

4: 92 percent / pyridine

With pyridine; sodium tetrahydroborate; cerium(III) chloride; iodine; sodium hydride; In methanol; 1,2-dimethoxyethane; water;

upstream raw materials:

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride

methyl 3-methylphenylacetate

dimethyl [3-(3-methylphenyl)-2-oxopropane]phosphonate

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

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