benzyl (2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)butanoate

Base Information

Chemical Name:benzyl (2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)butanoate
CAS No.:1607826-52-7
Molecular Formula:C₃₁H₃₄N₂O₆
Molecular Weight:530.621
Hs Code.:

Synonyms:benzyl (2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)butanoate

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Chemical Property of benzyl (2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)butanoate

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Technology Process of benzyl (2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)butanoate

There total 6 articles about benzyl (2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)butanoate 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: 84.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 1607826-51-6
benzyl (2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-azidobutanoate

: 1607826-52-7
benzyl (2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)butanoate

Guidance literature:: benzyl (2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-azidobutanoate; With tin(ll) chloride; In 1,4-dioxane; water; at 0 - 23 ℃; for 24h; Inert atmosphere;

di-tert-butyl dicarbonate; With sodium hydrogencarbonate; In 1,4-dioxane; water; at 0 - 23 ℃; for 15h; Inert atmosphere;
DOI:10.1021/ja502744a

Reference yield:

: benzyl 2-((tert-butoxycarbonyl)amino)-3-(((trifluoromethyl)sulfonyl)oxy)butanoate

: 1607826-52-7
benzyl (2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)butanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetrabutylammoniun azide / dichloromethane / 2.5 h / -78 - 25 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 2 h / 23 °C / Inert atmosphere

3.1: sodium hydroxide; N-ethyl-N,N-diisopropylamine / water; tetrahydrofuran / 3 h / 23 °C / Inert atmosphere

4.1: tin(ll) chloride / water; 1,4-dioxane / 24 h / 0 - 23 °C / Inert atmosphere

4.2: 15 h / 0 - 23 °C / Inert atmosphere

With tetrabutylammoniun azide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; tin(ll) chloride; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;
DOI:10.1021/ja502744a

Reference yield:

: 140422-54-4,33662-26-9
N-(tert-butyloxycarbonyl)-threonine benzyl ester

: 1607826-52-7
benzyl (2S,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)butanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 1.5 h / -78 °C / Inert atmosphere

2.1: tetrabutylammoniun azide / dichloromethane / 2.5 h / -78 - 25 °C / Inert atmosphere

3.1: trifluoroacetic acid / dichloromethane / 2 h / 23 °C / Inert atmosphere

4.1: sodium hydroxide; N-ethyl-N,N-diisopropylamine / water; tetrahydrofuran / 3 h / 23 °C / Inert atmosphere

5.1: tin(ll) chloride / water; 1,4-dioxane / 24 h / 0 - 23 °C / Inert atmosphere

5.2: 15 h / 0 - 23 °C / Inert atmosphere

With 2,6-dimethylpyridine; tetrabutylammoniun azide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; tin(ll) chloride; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;
DOI:10.1021/ja502744a