(2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4,8-bis-(tert-butyldimethylsilanyloxy)octanoic acid

Base Information

Chemical Name:(2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4,8-bis-(tert-butyldimethylsilanyloxy)octanoic acid
CAS No.:817166-94-2
Molecular Formula:C₃₂H₅₉NO₆Si₂
Molecular Weight:609.995
Hs Code.:

Synonyms:(2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4,8-bis-(tert-butyldimethylsilanyloxy)octanoic acid

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Chemical Property of (2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4,8-bis-(tert-butyldimethylsilanyloxy)octanoic acid

Chemical Property:

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Technology Process of (2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4,8-bis-(tert-butyldimethylsilanyloxy)octanoic acid

There total 11 articles about (2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4,8-bis-(tert-butyldimethylsilanyloxy)octanoic 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:

: 817166-96-4
[4-(tert-butyldimethylsilanyloxy)-(1S)-1-(5-oxotetrahydrofuran-(2R)-2-yl)butyl]carbamic acid tert-butyl ester

: 817166-94-2
(2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4,8-bis-(tert-butyldimethylsilanyloxy)octanoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: LDA / tetrahydrofuran; hexane / 3.5 h / -78 °C

2: Ac₂O; Et₃N / 1.25 h / Heating

3: 0.790 g / H₂ / Pd/C / ethyl acetate; methanol / 4.25 h

4: aq. LiOH / dioxane / 1 h / 20 °C

5: 0.266 g / imidazole / dimethylformamide / 50 h / 20 °C

With 1H-imidazole; lithium hydroxide; hydrogen; acetic anhydride; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ol047879y

Reference yield:

: 5-tert-butoxycarbonylamino-8-(tert-butyl-dimethyl-silanyloxy)-4-oxo-oct-2-enoic acid methyl ester

: 817166-94-2
(2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4,8-bis-(tert-butyldimethylsilanyloxy)octanoic acid

Guidance literature:: Multi-step reaction with 8 steps

1: 1.44 g / H₂ / Pd/C / ethyl acetate / 4 h

2: LiAlH(t-BuO)3 / ethanol / 2.5 h / -78 °C

3: 2.909 g / AcOH / toluene / 3 h / Heating

4: LDA / tetrahydrofuran; hexane / 3.5 h / -78 °C

5: Ac₂O; Et₃N / 1.25 h / Heating

6: 0.790 g / H₂ / Pd/C / ethyl acetate; methanol / 4.25 h

7: aq. LiOH / dioxane / 1 h / 20 °C

8: 0.266 g / imidazole / dimethylformamide / 50 h / 20 °C

With 1H-imidazole; lithium hydroxide; hydrogen; acetic anhydride; acetic acid; lithium tri-t-butoxyaluminum hydride; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol047879y

Reference yield:

: 817166-97-5
5-tert-butoxycarbonylamino-8-(tert-butyldimethylsilanyloxy)-4-oxooctanoic acid methyl ester

: 817166-94-2
(2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4,8-bis-(tert-butyldimethylsilanyloxy)octanoic acid

Guidance literature:: Multi-step reaction with 7 steps

1: LiAlH(t-BuO)3 / ethanol / 2.5 h / -78 °C

2: 2.909 g / AcOH / toluene / 3 h / Heating

3: LDA / tetrahydrofuran; hexane / 3.5 h / -78 °C

4: Ac₂O; Et₃N / 1.25 h / Heating

5: 0.790 g / H₂ / Pd/C / ethyl acetate; methanol / 4.25 h

6: aq. LiOH / dioxane / 1 h / 20 °C

7: 0.266 g / imidazole / dimethylformamide / 50 h / 20 °C

With 1H-imidazole; lithium hydroxide; hydrogen; acetic anhydride; acetic acid; lithium tri-t-butoxyaluminum hydride; triethylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol047879y