(3S)-6-(tert-butoxycarbonyl)-3-[N-(tert-butoxycarbonyl)amino]-4-oxo-hexanoic acid

Base Information

Chemical Name:(3S)-6-(tert-butoxycarbonyl)-3-[N-(tert-butoxycarbonyl)amino]-4-oxo-hexanoic acid
CAS No.:768395-86-4
Molecular Formula:C₁₆H₂₇NO₇
Molecular Weight:345.393
Hs Code.:

Synonyms:(3S)-6-(tert-butoxycarbonyl)-3-[N-(tert-butoxycarbonyl)amino]-4-oxo-hexanoic acid

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Chemical Property of (3S)-6-(tert-butoxycarbonyl)-3-[N-(tert-butoxycarbonyl)amino]-4-oxo-hexanoic acid

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Technology Process of (3S)-6-(tert-butoxycarbonyl)-3-[N-(tert-butoxycarbonyl)amino]-4-oxo-hexanoic acid

There total 2 articles about (3S)-6-(tert-butoxycarbonyl)-3-[N-(tert-butoxycarbonyl)amino]-4-oxo-hexanoic acid 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:

: 40856-59-5,132957-40-5
tert-butyl (3S)-2-oxotetrahydrofuran-3-ylcarbamate

: 768395-86-4
(3S)-6-(tert-butoxycarbonyl)-3-[N-(tert-butoxycarbonyl)amino]-4-oxo-hexanoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C

1.2: 48 percent / hexane; tetrahydrofuran / 1 h / -78 °C

2.1: 53 percent / lithium chloride; triethylamine / acetonitrile / 1 h / 0 °C

3.1: 59 percent / H₂ / Pd/C / ethyl acetate / 3 h / 20 °C

4.1: 62 percent / pyridinium dichromate / dimethylformamide / 2.5 h

With dipyridinium dichromate; n-butyllithium; hydrogen; triethylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; hexane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 2.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jm040780c

Reference yield:

: 7633-32-1
tert-butyl glyoxylate

: 768395-86-4
(3S)-6-(tert-butoxycarbonyl)-3-[N-(tert-butoxycarbonyl)amino]-4-oxo-hexanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 53 percent / lithium chloride; triethylamine / acetonitrile / 1 h / 0 °C

2: 59 percent / H₂ / Pd/C / ethyl acetate / 3 h / 20 °C

3: 62 percent / pyridinium dichromate / dimethylformamide / 2.5 h

With dipyridinium dichromate; hydrogen; triethylamine; lithium chloride; palladium on activated charcoal; In ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jm040780c

Reference yield: 72.0%

: 100-39-0
benzyl bromide

: 768395-86-4
(3S)-6-(tert-butoxycarbonyl)-3-[N-(tert-butoxycarbonyl)amino]-4-oxo-hexanoic acid

: 768395-88-6
benzyl (3R/S)-6-(tert-butoxycarbonyl)-3-[N-(tert-butoxycarbonyl)amino]-4-oxo-hexanoate

Guidance literature:: (3S)-6-(tert-butoxycarbonyl)-3-[N-(tert-butoxycarbonyl)amino]-4-oxo-hexanoic acid; With caesium carbonate; In methanol; pH=8;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 6h;
DOI:10.1021/jm040780c