(2R,4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-2-methyl-6-phenylhexanoic acid

Base Information

Chemical Name:(2R,4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-2-methyl-6-phenylhexanoic acid
CAS No.:123482-69-9
Molecular Formula:C₂₄H₄₁NO₅Si
Molecular Weight:451.679
Hs Code.:

Synonyms:(2R,4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-2-methyl-6-phenylhexanoic acid

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Chemical Property of (2R,4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-2-methyl-6-phenylhexanoic acid

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Technology Process of (2R,4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-2-methyl-6-phenylhexanoic acid

There total 6 articles about (2R,4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-2-methyl-6-phenylhexanoic 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:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 154160-25-5
(2R,4S,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-2-methyl-6-phenyl-hexanoic acid

: 123482-69-9
(2R,4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-2-methyl-6-phenylhexanoic acid

Guidance literature:: With 1H-imidazole; Multistep reaction; 1.) DMF, RT, 24 h, 2.) DMF, MeOH, RT, 4 h;
DOI:10.1021/jm00088a004

Reference yield:

: 133333-27-4
tert-butyl (1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate

: 123482-69-9
(2R,4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-2-methyl-6-phenylhexanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -78 °C

1.2: 79 percent / tetrahydrofuran / 0.5 h / -78 °C

2.1: aq. LiOH / dioxane / 3 h / 23 °C

3.1: imidazole / dimethylformamide / 12 h / 23 °C

With 1H-imidazole; lithium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide;
DOI:10.1021/jm0101803

Reference yield:

: 193338-94-2
(5S,1'S)-carbetoxy-5-<1-<<(1',1-dimethylothoxy)carbonyl>amino>-2-phenylmethyl>dihydrofuran-2(3H)-one

: 123482-69-9
(2R,4S,5S)-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-2-methyl-6-phenylhexanoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: NaOEt / ethanol / 18 h / Ambient temperature

2: aq. LiOH / ethanol / 5 h

3: toluene / 24 h / Heating

4: aq. LiOH / 1,2-dimethoxy-ethane / 3 h / Ambient temperature

5: 1.) imidazole / 1.) DMF, RT, 24 h, 2.) DMF, MeOH, RT, 4 h

With 1H-imidazole; lithium hydroxide; sodium ethanolate; In 1,2-dimethoxyethane; ethanol; toluene;
DOI:10.1021/jm00088a004