N-[(2S,5R)-6-(4-bromo-1-tosyl-1H-indol-3-yl)-5-hydroxy-2-[(triisopropylsilyloxy)methyl]hex-3-yn-1-yl]-4-methylbenzenesulfonamide

Base Information

• Chemical Name: N-[(2S,5R)-6-(4-bromo-1-tosyl-1H-indol-3-yl)-5-hydroxy-2-[(triisopropylsilyloxy)methyl]hex-3-yn-1-yl]-4-methylbenzenesulfonamide
• CAS No.: 1310737-20-2
• Molecular Formula: C₃₈H₄₉BrN₂O₆S₂Si
• Molecular Weight: 801.938

Synonyms:N-[(2S,5R)-6-(4-bromo-1-tosyl-1H-indol-3-yl)-5-hydroxy-2-[(triisopropylsilyloxy)methyl]hex-3-yn-1-yl]-4-methylbenzenesulfonamide

Chemical Property of N-[(2S,5R)-6-(4-bromo-1-tosyl-1H-indol-3-yl)-5-hydroxy-2-[(triisopropylsilyloxy)methyl]hex-3-yn-1-yl]-4-methylbenzenesulfonamide

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Technology Process of N-[(2S,5R)-6-(4-bromo-1-tosyl-1H-indol-3-yl)-5-hydroxy-2-[(triisopropylsilyloxy)methyl]hex-3-yn-1-yl]-4-methylbenzenesulfonamide

There total 3 articles about N-[(2S,5R)-6-(4-bromo-1-tosyl-1H-indol-3-yl)-5-hydroxy-2-[(triisopropylsilyloxy)methyl]hex-3-yn-1-yl]-4-methylbenzenesulfonamide 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: 52.0%

N-[(S)-4-[3-(4-bromo-1-tosyl-1H-indol-3-yl)oxiran-2-yl]-2-[(triisopropylsilyloxy)methyl]but-3-yn-1-yl]-4-methylbenzenesulfonamide → (S)-N-[6-(4-bromo-1-tosyl-1H-indol-3-yl)-5-oxo-2-[(triisopropylsilyloxy)methyl]hex-3-yn-1-yl]-4-methylbenzenesulfonamide (1310737-22-4) + N-[(2S,5S)-6-(4-bromo-1-tosyl-1H-indol-3-yl)-5-hydroxy-2-[(triisopropylsilyloxy)methyl]hex-3-yn-1-yl]-4-methylbenzenesulfonamide + N-[(2S,5R)-6-(4-bromo-1-tosyl-1H-indol-3-yl)-5-hydroxy-2-[(triisopropylsilyloxy)methyl]hex-3-yn-1-yl]-4-methylbenzenesulfonamide (1310737-20-2)

Guidance literature:

With zinc trifluoromethanesulfonate; sodium cyanoborohydride; In 1,4-dioxane; at 100 ℃; for 0.5h; regioselective reaction;

DOI:10.1021/jo2008324

Reference yield: 7.0%

N-[(S)-4-[3-(4-bromo-1-tosyl-1H-indol-3-yl)oxiran-2-yl]-2-[(triisopropylsilyloxy)methyl]but-3-yn-1-yl]-4-methylbenzenesulfonamide → (S)-N-[6-(4-bromo-1-tosyl-1H-indol-3-yl)-5-oxo-2-[(triisopropylsilyloxy)methyl]hex-3-yn-1-yl]-4-methylbenzenesulfonamide (1310737-22-4) + N-[(2S,5S)-6-(4-bromo-1-tosyl-1H-indol-3-yl)-5-hydroxy-2-[(triisopropylsilyloxy)methyl]hex-3-yn-1-yl]-4-methylbenzenesulfonamide + N-[(2S,5R)-6-(4-bromo-1-tosyl-1H-indol-3-yl)-5-hydroxy-2-[(triisopropylsilyloxy)methyl]hex-3-yn-1-yl]-4-methylbenzenesulfonamide (1310737-20-2) + N-[(2S,5R,Z)-6-(4-bromo-1-tosylindolin-3-ylidene)-5-hydroxy-2-[(triisopropylsilyloxy)methyl]hex-3-yn-1-yl]-4-methylbenzenesulfonamide (1310737-21-3)

Guidance literature:

N-[(S)-4-[3-(4-bromo-1-tosyl-1H-indol-3-yl)oxiran-2-yl]-2-[(triisopropylsilyloxy)methyl]but-3-yn-1-yl]-4-methylbenzenesulfonamide; With sodium cyanoborohydride; zinc(II) chloride; In tetrahydrofuran; diethyl ether; at 60 ℃; for 2.5h; Inert atmosphere;

With sodium hydrogencarbonate; In tetrahydrofuran; Saturated solution;

DOI:10.1021/jo2008324

Reference yield:

N-[(S)-4-[3-(4-bromo-1-tosyl-1H-indol-3-yl)oxiran-2-yl]-2-[(triisopropylsilyloxy)methyl]but-3-yn-1-yl]-4-methylbenzenesulfonamide → N-[(2S,5S)-6-(4-bromo-1-tosyl-1H-indol-3-yl)-5-hydroxy-2-[(triisopropylsilyloxy)methyl]hex-3-yn-1-yl]-4-methylbenzenesulfonamide + N-[(2S,5R)-6-(4-bromo-1-tosyl-1H-indol-3-yl)-5-hydroxy-2-[(triisopropylsilyloxy)methyl]hex-3-yn-1-yl]-4-methylbenzenesulfonamide (1310737-20-2)

Guidance literature:

With dimethylaluminum chloride; sodium cyanoborohydride; In tetrahydrofuran; at 60 ℃; for 0.25h; regioselective reaction;

DOI:10.1021/jo2008324

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