(R)-1-((3S,4S)-6-fluoro-9-(methylsulfonyl)-4-((E)-styryl)-1,3,4,9-tetrahydropyrano[3,4-b]indol-3-yl)-2-methoxyethanol

Base Information

• Chemical Name: (R)-1-((3S,4S)-6-fluoro-9-(methylsulfonyl)-4-((E)-styryl)-1,3,4,9-tetrahydropyrano[3,4-b]indol-3-yl)-2-methoxyethanol
• CAS No.: 1314595-97-5
• Molecular Formula: C₂₃H₂₄FNO₅S
• Molecular Weight: 445.512

Synonyms:(R)-1-((3S,4S)-6-fluoro-9-(methylsulfonyl)-4-((E)-styryl)-1,3,4,9-tetrahydropyrano[3,4-b]indol-3-yl)-2-methoxyethanol

Chemical Property of (R)-1-((3S,4S)-6-fluoro-9-(methylsulfonyl)-4-((E)-styryl)-1,3,4,9-tetrahydropyrano[3,4-b]indol-3-yl)-2-methoxyethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-((3S,4S)-6-fluoro-9-(methylsulfonyl)-4-((E)-styryl)-1,3,4,9-tetrahydropyrano[3,4-b]indol-3-yl)-2-methoxyethanol

There total 4 articles about (R)-1-((3S,4S)-6-fluoro-9-(methylsulfonyl)-4-((E)-styryl)-1,3,4,9-tetrahydropyrano[3,4-b]indol-3-yl)-2-methoxyethanol 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:

5-fluoro-2-((((2R,3S,6S)-2-(methoxymethyl)-6-phenyl-3,6-dihydro-2H-pyran-3-yl)oxy)methyl)-1-(methylsulfonyl)-1H-indole (1314595-84-0) → (R)-1-((3S,4S)-6-fluoro-9-(methylsulfonyl)-4-((E)-styryl)-1,3,4,9-tetrahydropyrano[3,4-b]indol-3-yl)-2-methoxyethanol (1314595-97-5) + (R)-1-((3S,4R)-6-fluoro-9-(methylsulfonyl)-4-((E)-styryl)-1,3,4,9-tetrahydropyrano[3,4-b]indol-3-yl)-2-methoxyethanol (1314595-98-6)

Guidance literature:

5-fluoro-2-((((2R,3S,6S)-2-(methoxymethyl)-6-phenyl-3,6-dihydro-2H-pyran-3-yl)oxy)methyl)-1-(methylsulfonyl)-1H-indole; With scandium tris(trifluoromethanesulfonate); In nitromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;

With water; sodium hydrogencarbonate; In nitromethane; for 0.166667h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol201532k

Reference yield:

C18H24O3Si → (R)-1-((3S,4S)-6-fluoro-9-(methylsulfonyl)-4-((E)-styryl)-1,3,4,9-tetrahydropyrano[3,4-b]indol-3-yl)-2-methoxyethanol (1314595-97-5) + (R)-1-((3S,4R)-6-fluoro-9-(methylsulfonyl)-4-((E)-styryl)-1,3,4,9-tetrahydropyrano[3,4-b]indol-3-yl)-2-methoxyethanol (1314595-98-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere

3.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diethylamine / 2 h / 50 °C

4.1: scandium tris(trifluoromethanesulfonate) / nitromethane / 3 h / 0 - 20 °C / Inert atmosphere

4.2: 0.17 h / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrabutyl ammonium fluoride; sodium hydride; diethylamine; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; nitromethane; mineral oil;

DOI:10.1021/ol201532k

Reference yield:

C15H22O3Si → (R)-1-((3S,4S)-6-fluoro-9-(methylsulfonyl)-4-((E)-styryl)-1,3,4,9-tetrahydropyrano[3,4-b]indol-3-yl)-2-methoxyethanol (1314595-97-5) + (R)-1-((3S,4R)-6-fluoro-9-(methylsulfonyl)-4-((E)-styryl)-1,3,4,9-tetrahydropyrano[3,4-b]indol-3-yl)-2-methoxyethanol (1314595-98-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere

4.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; diethylamine / 2 h / 50 °C

5.1: scandium tris(trifluoromethanesulfonate) / nitromethane / 3 h / 0 - 20 °C / Inert atmosphere

5.2: 0.17 h / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; tetrabutyl ammonium fluoride; sodium hydride; diethylamine; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; nitromethane; mineral oil;

DOI:10.1021/ol201532k

upstream raw materials:

5-fluoro-2-((((2R,3S,6S)-2-(methoxymethyl)-6-phenyl-3,6-dihydro-2H-pyran-3-yl)oxy)methyl)-1-(methylsulfonyl)-1H-indole

C₁₅H₁₆O₃

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