2-(trimethylsilyl)ethyl (4R)-4-[tert-butoxycarbonyl(methyl)amino]-5-(4-methoxyphenyl)-3-oxopentanoate

Base Information

Chemical Name:2-(trimethylsilyl)ethyl (4R)-4-[tert-butoxycarbonyl(methyl)amino]-5-(4-methoxyphenyl)-3-oxopentanoate
CAS No.:929872-82-2
Molecular Formula:C₂₃H₃₇NO₆Si
Molecular Weight:451.635
Hs Code.:

Synonyms:2-(trimethylsilyl)ethyl (4R)-4-[tert-butoxycarbonyl(methyl)amino]-5-(4-methoxyphenyl)-3-oxopentanoate

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Chemical Property of 2-(trimethylsilyl)ethyl (4R)-4-[tert-butoxycarbonyl(methyl)amino]-5-(4-methoxyphenyl)-3-oxopentanoate

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Technology Process of 2-(trimethylsilyl)ethyl (4R)-4-[tert-butoxycarbonyl(methyl)amino]-5-(4-methoxyphenyl)-3-oxopentanoate

There total 3 articles about 2-(trimethylsilyl)ethyl (4R)-4-[tert-butoxycarbonyl(methyl)amino]-5-(4-methoxyphenyl)-3-oxopentanoate 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: 97.0%

: tert-butyl (R)-3-(4-hydroxyphenyl)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl(methyl)carbamate

: 16046-10-9
2-(trimethylsilyl)ethyl acetate

: 929872-82-2
2-(trimethylsilyl)ethyl (4R)-4-[tert-butoxycarbonyl(methyl)amino]-5-(4-methoxyphenyl)-3-oxopentanoate

Guidance literature:: 2-(trimethylsilyl)ethyl acetate; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

tert-butyl (R)-3-(4-hydroxyphenyl)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl(methyl)carbamate; In tetrahydrofuran; at -78 - 20 ℃; Further stages.;
DOI:10.1055/s-2006-958931

Reference yield:

: 929872-80-0
tert-butyl (R)-3-(4-hydroxyphenyl)-1-[methoxy(methyl)amino]-1-oxopropan-2-ylcarbamate

: 929872-82-2
2-(trimethylsilyl)ethyl (4R)-4-[tert-butoxycarbonyl(methyl)amino]-5-(4-methoxyphenyl)-3-oxopentanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide / -20 °C

1.2: 75 percent / dimethylformamide / 3 h / -20 °C

2.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

2.2: 97 percent / tetrahydrofuran / -78 - 20 °C

With sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1055/s-2006-958931

Reference yield:

: 70642-86-3
N-(tert-butoxycarbonyl)-D-tyrosine

: 929872-82-2
2-(trimethylsilyl)ethyl (4R)-4-[tert-butoxycarbonyl(methyl)amino]-5-(4-methoxyphenyl)-3-oxopentanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 87 percent / DCC; DMAP; Et₃N / CH₂Cl₂ / 4 h / 20 °C

2.1: NaH / dimethylformamide / -20 °C

2.2: 75 percent / dimethylformamide / 3 h / -20 °C

3.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

3.2: 97 percent / tetrahydrofuran / -78 - 20 °C

With dmap; sodium hydride; triethylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-2006-958931