N-benzyl-N-[(E)-(R)-1-((S)-1-hydroxy-3-trimethylsilylprop-2-ynyl)-4-(4-methoxybenzyloxy)but-2-enyl]-4-methylbenzenesulfonamide

Base Information

Chemical Name:N-benzyl-N-[(E)-(R)-1-((S)-1-hydroxy-3-trimethylsilylprop-2-ynyl)-4-(4-methoxybenzyloxy)but-2-enyl]-4-methylbenzenesulfonamide
CAS No.:1029537-49-2
Molecular Formula:C₃₂H₃₉NO₅SSi
Molecular Weight:577.817
Hs Code.:

Synonyms:N-benzyl-N-[(E)-(R)-1-((S)-1-hydroxy-3-trimethylsilylprop-2-ynyl)-4-(4-methoxybenzyloxy)but-2-enyl]-4-methylbenzenesulfonamide

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Chemical Property of N-benzyl-N-[(E)-(R)-1-((S)-1-hydroxy-3-trimethylsilylprop-2-ynyl)-4-(4-methoxybenzyloxy)but-2-enyl]-4-methylbenzenesulfonamide

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Technology Process of N-benzyl-N-[(E)-(R)-1-((S)-1-hydroxy-3-trimethylsilylprop-2-ynyl)-4-(4-methoxybenzyloxy)but-2-enyl]-4-methylbenzenesulfonamide

There total 10 articles about N-benzyl-N-[(E)-(R)-1-((S)-1-hydroxy-3-trimethylsilylprop-2-ynyl)-4-(4-methoxybenzyloxy)but-2-enyl]-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%

: C₃₂H₃₉NO₅SSi

: N-benzyl-N-[(R)-1-((S)-1-hydroxy-3-trimethylsilylprop-2-ynyl)-4-(4-methoxybenzyloxy)but-2-enyl]-4-methylbenzenesulfonamide

: 1029537-49-2
N-benzyl-N-[(E)-(R)-1-((S)-1-hydroxy-3-trimethylsilylprop-2-ynyl)-4-(4-methoxybenzyloxy)but-2-enyl]-4-methylbenzenesulfonamide

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h; stereoselective reaction;
DOI:10.1002/chem.201003265

Reference yield:

: C₂₈H₃₂O₃Si

: N-benzyl-N-[(R)-1-((S)-1-hydroxy-3-trimethylsilylprop-2-ynyl)-4-(4-methoxybenzyloxy)but-2-enyl]-4-methylbenzenesulfonamide

: 1029537-49-2
N-benzyl-N-[(E)-(R)-1-((S)-1-hydroxy-3-trimethylsilylprop-2-ynyl)-4-(4-methoxybenzyloxy)but-2-enyl]-4-methylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: N-Bromosuccinimide; silver nitrate / acetone / 12 h / 20 °C / Darkness

2.1: potassium phosphate; copper(ll) sulfate pentahydrate; 1,10-Phenanthroline / toluene / 8 h / 65 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

4.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 0.25 h / 20 °C

5.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / water; toluene / 0.5 h / 20 °C

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C

6.2: -78 - 20 °C

7.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.17 h / -78 °C

With potassium phosphate; N-Bromosuccinimide; n-butyllithium; 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydrogensulfate; silver nitrate; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; hexane; water; acetone; toluene; 7.1: Wittig rearrangement;
DOI:10.1002/chem.201003265

Reference yield:

: 1300116-86-2
(3R)-1-bromo-3-[(tert-butyldiphenylsilyl)oxy]-4-(4-methoxybenzyloxy)but-1-yne

: N-benzyl-N-[(R)-1-((S)-1-hydroxy-3-trimethylsilylprop-2-ynyl)-4-(4-methoxybenzyloxy)but-2-enyl]-4-methylbenzenesulfonamide

: 1029537-49-2
N-benzyl-N-[(E)-(R)-1-((S)-1-hydroxy-3-trimethylsilylprop-2-ynyl)-4-(4-methoxybenzyloxy)but-2-enyl]-4-methylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: potassium phosphate; copper(ll) sulfate pentahydrate; 1,10-Phenanthroline / toluene / 8 h / 65 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 0.25 h / 20 °C

4.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / water; toluene / 0.5 h / 20 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C

5.2: -78 - 20 °C

6.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.17 h / -78 °C

With potassium phosphate; n-butyllithium; 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydrogensulfate; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; hexane; water; toluene; 6.1: Wittig rearrangement;
DOI:10.1002/chem.201003265