tert-butyl (2S,4R)-6-azido-2-[(tert-butoxycarbonyl)amino]-4-{[tert-butyl(diphenyl)silyl]oxy}hexanoate

Base Information

Chemical Name:tert-butyl (2S,4R)-6-azido-2-[(tert-butoxycarbonyl)amino]-4-{[tert-butyl(diphenyl)silyl]oxy}hexanoate
CAS No.:653589-54-9
Molecular Formula:C₃₁H₄₆N₄O₅Si
Molecular Weight:582.816
Hs Code.:

Synonyms:tert-butyl (2S,4R)-6-azido-2-[(tert-butoxycarbonyl)amino]-4-{[tert-butyl(diphenyl)silyl]oxy}hexanoate

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Chemical Property of tert-butyl (2S,4R)-6-azido-2-[(tert-butoxycarbonyl)amino]-4-{[tert-butyl(diphenyl)silyl]oxy}hexanoate

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Technology Process of tert-butyl (2S,4R)-6-azido-2-[(tert-butoxycarbonyl)amino]-4-{[tert-butyl(diphenyl)silyl]oxy}hexanoate

There total 6 articles about tert-butyl (2S,4R)-6-azido-2-[(tert-butoxycarbonyl)amino]-4-{[tert-butyl(diphenyl)silyl]oxy}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:

: 2-tert-butoxycarbonylamino-4-(tert-butyl-diphenyl-silanyloxy)-6-methanesulfonyloxy-hexanoic acid tert-butyl ester

: 653589-54-9
tert-butyl (2S,4R)-6-azido-2-[(tert-butoxycarbonyl)amino]-4-{[tert-butyl(diphenyl)silyl]oxy}hexanoate

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 8h;
DOI:10.1021/jo0353886

Reference yield:

: 34582-32-6
N-tert-butoxycarbonyl aspartic acid tert-butyl ester

: 653589-54-9
tert-butyl (2S,4R)-6-azido-2-[(tert-butoxycarbonyl)amino]-4-{[tert-butyl(diphenyl)silyl]oxy}hexanoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 3 h / 0 - 20 °C

1.2: 77 percent / ethyl acetate / 5 h / Heating

2.1: NaBH₃CN; acetic acid / CH₂Cl₂ / 72 h / 20 °C

3.1: 88 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

4.1: 97 percent / NaBH₄ / ethanol / 0 - 20 °C

5.1: diisopropylethylamine / CH₂Cl₂ / 3 h / 0 - 20 °C

6.1: 560 mg / NaN₃ / dimethylformamide / 8 h / 80 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; sodium azide; sodium cyanoborohydride; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo0353886

Reference yield:

: 653589-10-7
1,2-di-tert-butyl (2S)-4,6-dioxopiperidine-1,2-dicarboxylate

: 653589-54-9
tert-butyl (2S,4R)-6-azido-2-[(tert-butoxycarbonyl)amino]-4-{[tert-butyl(diphenyl)silyl]oxy}hexanoate

Guidance literature:: Multi-step reaction with 5 steps

1: NaBH₃CN; acetic acid / CH₂Cl₂ / 72 h / 20 °C

2: 88 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

3: 97 percent / NaBH₄ / ethanol / 0 - 20 °C

4: diisopropylethylamine / CH₂Cl₂ / 3 h / 0 - 20 °C

5: 560 mg / NaN₃ / dimethylformamide / 8 h / 80 °C

With 1H-imidazole; sodium tetrahydroborate; sodium azide; sodium cyanoborohydride; acetic acid; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo0353886