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

Base Information

Chemical Name:benzyl (3R/S)-6-(tert-butoxycarbonyl)-3-[N-(tert-butoxycarbonyl)amino]-4-oxo-hexanoate
CAS No.:768395-88-6
Molecular Formula:C₂₃H₃₃NO₇
Molecular Weight:435.518
Hs Code.:

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

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Chemical Property of benzyl (3R/S)-6-(tert-butoxycarbonyl)-3-[N-(tert-butoxycarbonyl)amino]-4-oxo-hexanoate

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Technology Process of benzyl (3R/S)-6-(tert-butoxycarbonyl)-3-[N-(tert-butoxycarbonyl)amino]-4-oxo-hexanoate

There total 7 articles about benzyl (3R/S)-6-(tert-butoxycarbonyl)-3-[N-(tert-butoxycarbonyl)amino]-4-oxo-hexanoate 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: 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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

5.1: aq. Cs₂CO₃ / methanol / pH 8

5.2: 72 percent / dimethylformamide / 6 h / 20 °C

With dipyridinium dichromate; n-butyllithium; hydrogen; caesium carbonate; triethylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; 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

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

Guidance literature:: Multi-step reaction with 4 steps

1.1: 53 percent / lithium chloride; triethylamine / acetonitrile / 1 h / 0 °C

2.1: 59 percent / H₂ / Pd/C / ethyl acetate / 3 h / 20 °C

3.1: 62 percent / pyridinium dichromate / dimethylformamide / 2.5 h

4.1: aq. Cs₂CO₃ / methanol / pH 8

4.2: 72 percent / dimethylformamide / 6 h / 20 °C

With dipyridinium dichromate; hydrogen; caesium carbonate; triethylamine; lithium chloride; palladium on activated charcoal; In methanol; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jm040780c