N-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-hydroxy-pentyl}-4-methyl-benzenesulfonamide

Base Information

• Chemical Name: N-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-hydroxy-pentyl}-4-methyl-benzenesulfonamide
• CAS No.: 934472-09-0
• Molecular Formula: C₂₀H₃₇NO₄SSi
• Molecular Weight: 415.67
• Mol file: 934472-09-0.mol

Synonyms:N-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-hydroxy-pentyl}-4-methyl-benzenesulfonamide

Chemical Property of N-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-hydroxy-pentyl}-4-methyl-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-hydroxy-pentyl}-4-methyl-benzenesulfonamide

There total 5 articles about N-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-hydroxy-pentyl}-4-methyl-benzenesulfonamide 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: 82.0%

N-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-pent-4-enyl}-4-methyl-benzenesulfonamide (934472-08-9) → N-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-hydroxy-pentyl}-4-methyl-benzenesulfonamide (934472-09-0)

Guidance literature:

N-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-pent-4-enyl}-4-methyl-benzenesulfonamide; With dimethylsulfide borane complex; In tetrahydrofuran; at -10 - 20 ℃; for 8h;

With sodium hydroxide; dihydrogen peroxide; at 0 - 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2007.01.082

Reference yield:

2-hydroxyethyl-1-(toluene-4-sulfonyl)aziridine (934472-06-7) → N-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-hydroxy-pentyl}-4-methyl-benzenesulfonamide (934472-09-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: imidazole / tetrahydrofuran / 8 h / 0 - 20 °C

2.1: 82 percent / tetrahydrofuran; diethyl ether / 6 h / -78 - 20 °C

3.1: BH₃*DMS / tetrahydrofuran / 8 h / -10 - 20 °C

3.2: 82 percent / H₂O₂; NaOH / 2 h / 0 - 20 °C

With 1H-imidazole; dimethylsulfide borane complex; In tetrahydrofuran; diethyl ether;

DOI:10.1016/j.tetlet.2007.01.082

Reference yield:

N-(3-hydroxy-1-hydroxymethyl-propyl)-4-methylbenzenesulfonamide (147136-78-5) → N-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-hydroxy-pentyl}-4-methyl-benzenesulfonamide (934472-09-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1,1'-(azodicarbonyl)dipiperidine; n-Bu₃P / toluene / 16 h / 0 - 20 °C

2.1: imidazole / tetrahydrofuran / 8 h / 0 - 20 °C

3.1: 82 percent / tetrahydrofuran; diethyl ether / 6 h / -78 - 20 °C

4.1: BH₃*DMS / tetrahydrofuran / 8 h / -10 - 20 °C

4.2: 82 percent / H₂O₂; NaOH / 2 h / 0 - 20 °C

With 1H-imidazole; tributylphosphine; dimethylsulfide borane complex; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; diethyl ether; toluene; 1.1: Mitsunobu condensation;

DOI:10.1016/j.tetlet.2007.01.082

upstream raw materials:

N-{1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-pent-4-enyl}-4-methyl-benzenesulfonamide

2-hydroxyethyl-1-(toluene-4-sulfonyl)aziridine

N-(3-hydroxy-1-hydroxymethyl-propyl)-4-methylbenzenesulfonamide

2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-(toluene-4-sulfonyl)-aziridine

Downstream raw materials:

[2R-(2S)]-phenylmethyl 2-(2-hydroxyheptyl)piperidinecarboxylate

[2R-(2R)]-phenylmethyl 2-(2-hydroxyheptyl)piperidinecarboxylate

[2R-(2S)]-phenylmethyl 2-(2-hydroxypent-4-enyl)piperidinecarboxylate

[2R-(2S)]-1-benzyloxycarbonyl-2-(2-hydroxypropyl)piperidine