benzyl (1S)-1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-oxo-undec-3-ynylcarbamate

Base Information

• Chemical Name: benzyl (1S)-1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-oxo-undec-3-ynylcarbamate
• CAS No.: 686722-16-7
• Molecular Formula: C₂₇H₄₃NO₄Si
• Molecular Weight: 473.728
• Mol file: 686722-16-7.mol

Synonyms:benzyl (1S)-1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-oxo-undec-3-ynylcarbamate

Chemical Property of benzyl (1S)-1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-oxo-undec-3-ynylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (1S)-1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-oxo-undec-3-ynylcarbamate

There total 4 articles about benzyl (1S)-1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-oxo-undec-3-ynylcarbamate 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:

benzyl (3S)-2-oxotetrahydro-3-furanylcarbamate (35677-89-5) → benzyl (1S)-1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-oxo-undec-3-ynylcarbamate (686722-16-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 77 percent / trimethylaluminum; pyridine / CH₂Cl₂; hexane / 72 h / 20 °C

2.1: 84 percent / imidazole / dimethylformamide / 16 h / 20 °C

3.1: n-BuLi / hexane; tetrahydrofuran / 2 h / -20 °C

3.2: tetrahydrofuran / 3 h / -78 - -40 °C

With pyridine; 1H-imidazole; n-butyllithium; trimethylaluminum; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo011062q

Reference yield:

1-nonyne (3452-09-3) + (2S)-2-{[1-(benzyloxy)vinyl]amino}-4-{[tert-butyl(dimethyl)silyl]oxy}-N-methoxy-N-methylbutanamide (177839-62-2) → benzyl (1S)-1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-oxo-undec-3-ynylcarbamate (686722-16-7)

Guidance literature:

1-nonyne; With n-butyllithium; In tetrahydrofuran; hexane; at -20 ℃; for 2h;

(2S)-2-{[1-(benzyloxy)vinyl]amino}-4-{[tert-butyl(dimethyl)silyl]oxy}-N-methoxy-N-methylbutanamide; In tetrahydrofuran; at -78 - -40 ℃; for 3h; Further stages.;

DOI:10.1021/jo011062q

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → benzyl (1S)-1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-oxo-undec-3-ynylcarbamate (686722-16-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 84 percent / imidazole / dimethylformamide / 16 h / 20 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 2 h / -20 °C

2.2: tetrahydrofuran / 3 h / -78 - -40 °C

With 1H-imidazole; n-butyllithium; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1021/jo011062q

upstream raw materials:

1-nonyne

(2S)-2-{[1-(benzyloxy)vinyl]amino}-4-{[tert-butyl(dimethyl)silyl]oxy}-N-methoxy-N-methylbutanamide

tert-butyldimethylsilyl chloride

benzyl (3S)-2-oxotetrahydro-3-furanylcarbamate