N-{(2S)-1-[(tert-butyldiphenylsilyl)oxy]-5-hydroxyhept-6-yn-2-yl}-4-methylbenzenesulfonamide

Base Information

• Chemical Name: N-{(2S)-1-[(tert-butyldiphenylsilyl)oxy]-5-hydroxyhept-6-yn-2-yl}-4-methylbenzenesulfonamide
• CAS No.: 1500059-25-5
• Molecular Formula: C₃₀H₃₇NO₄SSi
• Molecular Weight: 535.78
• Mol file: 1500059-25-5.mol

Synonyms:N-{(2S)-1-[(tert-butyldiphenylsilyl)oxy]-5-hydroxyhept-6-yn-2-yl}-4-methylbenzenesulfonamide

Chemical Property of N-{(2S)-1-[(tert-butyldiphenylsilyl)oxy]-5-hydroxyhept-6-yn-2-yl}-4-methylbenzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{(2S)-1-[(tert-butyldiphenylsilyl)oxy]-5-hydroxyhept-6-yn-2-yl}-4-methylbenzenesulfonamide

There total 5 articles about N-{(2S)-1-[(tert-butyldiphenylsilyl)oxy]-5-hydroxyhept-6-yn-2-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: 81.0%

N-p-toluenesulphonyl(5-diphenyl-tert-butylsilyloxymethyl)-2-hydroxypyrrolidine (143264-72-6,143292-32-4) + acetylenemagnesium bromide (4301-14-8) → N-{(2S)-1-[(tert-butyldiphenylsilyl)oxy]-5-hydroxyhept-6-yn-2-yl}-4-methylbenzenesulfonamide (1500059-25-5)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at -78 - 20 ℃; for 40h; Inert atmosphere;

DOI:10.1002/chem.201300687

Reference yield:

(S)-Pyroglutaminol (17342-08-4) → N-{(2S)-1-[(tert-butyldiphenylsilyl)oxy]-5-hydroxyhept-6-yn-2-yl}-4-methylbenzenesulfonamide (1500059-25-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 68 h / 20 °C / Inert atmosphere

2.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 1 h / -20 °C / Inert atmosphere

2.2: 17 h / -20 - 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / toluene; dichloromethane / 15 h / -78 - 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / tetrahydrofuran / 40 h / -78 - 20 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; diisobutylaluminium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/chem.201300687

Reference yield:

(-)-(5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosylpyrrolidin-2-one (132974-84-6) → N-{(2S)-1-[(tert-butyldiphenylsilyl)oxy]-5-hydroxyhept-6-yn-2-yl}-4-methylbenzenesulfonamide (1500059-25-5)

Guidance literature:

Multi-step reaction with 2 steps

1: diisobutylaluminium hydride / toluene; dichloromethane / 15 h / -78 - 20 °C / Inert atmosphere

2: diisobutylaluminium hydride / tetrahydrofuran / 40 h / -78 - 20 °C / Inert atmosphere

With diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1002/chem.201300687

upstream raw materials:

(-)-(5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosylpyrrolidin-2-one

(5S)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]pyrrolidin-2-one

N-p-toluenesulphonyl(5-diphenyl-tert-butylsilyloxymethyl)-2-hydroxypyrrolidine

acetylenemagnesium bromide

Downstream raw materials:

(2S,5R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-5-ethynyl-1-tosylpyrrolidine

C₃₀H₃₅NO₃SSi