(S)-N-(5-((tert-butyldimethylsilyl)oxy)-2-methylenepentyl)-N-glycidyl-2-nitrobenzenesulfonamide

Base Information

• Chemical Name: (S)-N-(5-((tert-butyldimethylsilyl)oxy)-2-methylenepentyl)-N-glycidyl-2-nitrobenzenesulfonamide
• CAS No.: 1609184-04-4
• Molecular Formula: C₂₁H₃₄N₂O₆SSi
• Molecular Weight: 470.662
• Mol file: 1609184-04-4.mol

Synonyms:(S)-N-(5-((tert-butyldimethylsilyl)oxy)-2-methylenepentyl)-N-glycidyl-2-nitrobenzenesulfonamide

Chemical Property of (S)-N-(5-((tert-butyldimethylsilyl)oxy)-2-methylenepentyl)-N-glycidyl-2-nitrobenzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-(5-((tert-butyldimethylsilyl)oxy)-2-methylenepentyl)-N-glycidyl-2-nitrobenzenesulfonamide

There total 3 articles about (S)-N-(5-((tert-butyldimethylsilyl)oxy)-2-methylenepentyl)-N-glycidyl-2-nitrobenzenesulfonamide 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: 86.0%

5-((tert-butyldimethylsilyl)oxy)-2-methylenepentan-1-ol (1071056-81-9) + N-glycidyl-2-nitrobenzenesulfonamide → (S)-N-(5-((tert-butyldimethylsilyl)oxy)-2-methylenepentyl)-N-glycidyl-2-nitrobenzenesulfonamide (1609184-04-4)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 20 ℃; for 0.666667h; Inert atmosphere;

DOI:10.1021/ol5010033

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (S)-N-(5-((tert-butyldimethylsilyl)oxy)-2-methylenepentyl)-N-glycidyl-2-nitrobenzenesulfonamide (1609184-04-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1H-imidazole / dichloromethane / 1 h / 20 °C / Inert atmosphere

2.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / diethyl ether / 24 h / -78 - 20 °C / Inert atmosphere

2.2: 11 h / -78 °C / Inert atmosphere

3.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 0.67 h / 20 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 3.1: |Mitsunobu Displacement;

DOI:10.1021/ol5010033

Reference yield:

N-allyloxycarbonyl-N-glycidyl-2-nitorobenzenesulfonamide → (S)-N-(5-((tert-butyldimethylsilyl)oxy)-2-methylenepentyl)-N-glycidyl-2-nitrobenzenesulfonamide (1609184-04-4)

Guidance literature:

Multi-step reaction with 2 steps

1: HSiPh₃; tetrakis(triphenylphosphine) palladium⁽⁰⁾; acetic acid / 1 h / 20 °C / Inert atmosphere

2: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 0.67 h / 20 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; acetic acid; triphenylphosphine; diethylazodicarboxylate; HSiPh₃; In tetrahydrofuran; toluene; 2: |Mitsunobu Displacement;

DOI:10.1021/ol5010033

upstream raw materials:

tert-butyldimethylsilyl chloride

5-((tert-butyldimethylsilyl)oxy)-2-methylenepentan-1-ol

Downstream raw materials:

(S)-N-glycidyl-N-(5-hydroxy-2-methylenepentyl)-2-nitrobenzenesulfonamide

(S)-N-(5-(N-allyloxycarbonyl-2-nitrobenzenesulfonamido)-2-methylenepentyl)-N-glycidyl-2-nitrobenzenesulfonamide

(S)-N-glycidyl-N-(2-methylene-5-(2-nitrobenzenesulfonamido)pentyl)-2-nitrobenzenesulfonamide

(R)-7-methylene-1,5-bis((2-nitrobenzene)sulfonyl)-1,5-diazecan-3-ol