(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid ethyl ester

Base Information

Chemical Name:(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid ethyl ester
CAS No.:936226-69-6
Molecular Formula:C₂₄H₄₁NO₅Si
Molecular Weight:451.679
Hs Code.:

Synonyms:(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid ethyl ester

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Chemical Property of (3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid ethyl ester

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Technology Process of (3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid ethyl ester

There total 8 articles about (3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid ethyl ester 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: 100.0%

: 72155-47-6
N-(tert-butoxycarbonyl)-4(S)-amino-3(R)-hydroxy-5-phenylpentanoic acid ethyl ester

: 18162-48-6
tert-butyldimethylsilyl chloride

: 936226-69-6
(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid ethyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide;
DOI:10.1016/0040-4039(96)00592-8

Reference yield:

: 1161-13-3
N-Cbz-L-Phe

: 936226-69-6
(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: pTSA

2: 96 percent / toluene / 3 h / Heating

3: 98 percent / H₂; trifluoroacetic acid / Pd/C / methanol / 2 h / 20 °C

4: 92 percent / Et₃N / methanol / 8 h / 20 °C

5: NaBH₄ / methanol / 1 h / 0 - 20 °C

6: 95 percent / imid / dimethylformamide / 10 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; hydrogen; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide; toluene; 1: Condensation / 2: Alkylation / 3: Hydrogenolysis / 4: Acylation / 5: Reduction / 6: silylation;
DOI:10.1246/cl.1999.703

Reference yield:

: 55740-07-3
(4S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester

: 936226-69-6
(3R,4S)-4-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / toluene / 3 h / Heating

2: 98 percent / H₂; trifluoroacetic acid / Pd/C / methanol / 2 h / 20 °C

3: 92 percent / Et₃N / methanol / 8 h / 20 °C

4: NaBH₄ / methanol / 1 h / 0 - 20 °C

5: 95 percent / imid / dimethylformamide / 10 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; hydrogen; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide; toluene; 1: Alkylation / 2: Hydrogenolysis / 3: Acylation / 4: Reduction / 5: silylation;
DOI:10.1246/cl.1999.703