5-benzyl-2-((1RS)-1-benzyl-2-{[(tert-butyl)(dimethyl)silyl]oxy}ethyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

Base Information

Chemical Name:5-benzyl-2-((1RS)-1-benzyl-2-{[(tert-butyl)(dimethyl)silyl]oxy}ethyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide
CAS No.:855780-70-0
Molecular Formula:C₂₇H₃₉N₃O₃SSi
Molecular Weight:513.776
Hs Code.:

Synonyms:5-benzyl-2-((1RS)-1-benzyl-2-{[(tert-butyl)(dimethyl)silyl]oxy}ethyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

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Chemical Property of 5-benzyl-2-((1RS)-1-benzyl-2-{[(tert-butyl)(dimethyl)silyl]oxy}ethyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

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Technology Process of 5-benzyl-2-((1RS)-1-benzyl-2-{[(tert-butyl)(dimethyl)silyl]oxy}ethyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

There total 5 articles about 5-benzyl-2-((1RS)-1-benzyl-2-{[(tert-butyl)(dimethyl)silyl]oxy}ethyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide 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: 67.0%

: 765951-42-6
2-((1RS)-1-benzyl-2-{[(tert-butyl)(dimethyl)silyl]oxy}ethyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

: 100-39-0
benzyl bromide

: 855780-70-0
5-benzyl-2-((1RS)-1-benzyl-2-{[(tert-butyl)(dimethyl)silyl]oxy}ethyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

Guidance literature:: 2-((1RS)-1-benzyl-2-{[(tert-butyl)(dimethyl)silyl]oxy}ethyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide; With sec.-butyllithium; In tetrahydrofuran; cyclohexane; at -78 ℃; for 0.5h;

benzyl bromide; In tetrahydrofuran; cyclohexane; at -78 - 20 ℃; for 3h;
DOI:10.1002/hlca.200590050

Reference yield:

: 765951-41-5
2-[(E)-1-formyl-2-phenylethenyl]-N,N-dimethyl-1H-imidazole-1-sulfonamide

: 855780-70-0
5-benzyl-2-((1RS)-1-benzyl-2-{[(tert-butyl)(dimethyl)silyl]oxy}ethyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: 82 percent / Bu₃SnH; AcOH / [Pd(PPh₃)4] / benzene / 14 h / 20 °C

2.1: 79 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / 20 °C

3.1: s-BuLi / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C

3.2: 67 percent / tetrahydrofuran; cyclohexane / 3 h / -78 - 20 °C

With dmap; sec.-butyllithium; tri-n-butyl-tin hydride; acetic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; cyclohexane; benzene;
DOI:10.1002/hlca.200590050

Reference yield:

: 33603-90-6
(2Z)-2-bromo-3-phenyl-2-propenal

: 855780-70-0
5-benzyl-2-((1RS)-1-benzyl-2-{[(tert-butyl)(dimethyl)silyl]oxy}ethyl)-N,N-dimethyl-1H-imidazole-1-sulfonamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: 50 percent / Ag₂O / [PdCl₂(PPh₃)2] / dimethylformamide / 48 h / 100 °C

2.1: 82 percent / Bu₃SnH; AcOH / [Pd(PPh₃)4] / benzene / 14 h / 20 °C

3.1: 79 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / 20 °C

4.1: s-BuLi / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C

4.2: 67 percent / tetrahydrofuran; cyclohexane / 3 h / -78 - 20 °C

With dmap; sec.-butyllithium; tri-n-butyl-tin hydride; acetic acid; silver(l) oxide; bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; cyclohexane; N,N-dimethyl-formamide; benzene; 1.1: Stille cross-coupling;
DOI:10.1002/hlca.200590050