benzyl (S)-2-(((allyloxy)carbonyl)amino)-5-((tertbutyldimethylsilyl)oxy)pentanoate

Base Information

Chemical Name:benzyl (S)-2-(((allyloxy)carbonyl)amino)-5-((tertbutyldimethylsilyl)oxy)pentanoate
CAS No.:500145-45-9
Molecular Formula:C₂₂H₃₅NO₅Si
Molecular Weight:421.609
Hs Code.:

Synonyms:benzyl (S)-2-(((allyloxy)carbonyl)amino)-5-((tertbutyldimethylsilyl)oxy)pentanoate

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Chemical Property of benzyl (S)-2-(((allyloxy)carbonyl)amino)-5-((tertbutyldimethylsilyl)oxy)pentanoate

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Technology Process of benzyl (S)-2-(((allyloxy)carbonyl)amino)-5-((tertbutyldimethylsilyl)oxy)pentanoate

There total 4 articles about benzyl (S)-2-(((allyloxy)carbonyl)amino)-5-((tertbutyldimethylsilyl)oxy)pentanoate 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: 94.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 500145-43-7
benzyl (S)-2-(((allyloxy)carbonyl)amino)-5-hydroxypentanoate

: 500145-45-9
benzyl (S)-2-(((allyloxy)carbonyl)amino)-5-((tertbutyldimethylsilyl)oxy)pentanoate

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(02)02178-0

Reference yield:

: Aloc-(S)-Glu-OBzl

: 500145-45-9
benzyl (S)-2-(((allyloxy)carbonyl)amino)-5-((tertbutyldimethylsilyl)oxy)pentanoate

Guidance literature:: Multi-step reaction with 3 steps

1: Et₃N / tetrahydrofuran

2: NaBH₄ / H₂O

3: 94 percent / imidazole / dimethylformamide

With 1H-imidazole; sodium tetrahydroborate; triethylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(02)02178-0

Reference yield:

: 13030-09-6
1-benzyl L-glutamate

: 500145-45-9
benzyl (S)-2-(((allyloxy)carbonyl)amino)-5-((tertbutyldimethylsilyl)oxy)pentanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydrogencarbonate / water; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

2.1: chloroformic acid ethyl ester; triethylamine / tetrahydrofuran / 4.5 h / -10 °C / Inert atmosphere

2.2: 4.25 h / -10 - 20 °C / Inert atmosphere

3.1: 1H-imidazole / N,N-dimethyl-formamide / 11 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; chloroformic acid ethyl ester; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/acs.joc.5b02386