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

Base Information

Chemical Name:(2R,4S,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-2-methyl-6-phenyl-hexanoic acid
CAS No.:154160-25-5
Molecular Formula:C₁₈H₂₇NO₅
Molecular Weight:337.416
Hs Code.:

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

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Chemical Property of (2R,4S,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-2-methyl-6-phenyl-hexanoic acid

Chemical Property:

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Technology Process of (2R,4S,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-2-methyl-6-phenyl-hexanoic acid

There total 17 articles about (2R,4S,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-2-methyl-6-phenyl-hexanoic 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:

: 104293-55-2
(3R,5S,1'S)-5-<1-<<(tert-butyloxy)carbonyl>amino>-2-phenylethyl>-3-methyldihydrofuran-2(3H)-one

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

Guidance literature:: With lithium hydroxide; In 1,2-dimethoxyethane; for 3h; Ambient temperature;
DOI:10.1021/jm00088a004

Reference yield:

: 95437-43-7
(S)-2-(N,N-dibenzylamino)-3-phenylpropanoic acid

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

Guidance literature:: Multi-step reaction with 9 steps

1: 92 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide*HCl, hydroxybenztriazole hydrate, DMAP, Hunig's base / dimethylformamide / 2 h / Ambient temperature

2: 93 percent / tetrahydrofuran / 0 °C

3: NaBH₄ / methanol / 0 °C

4: 92 percent / 3N HCl / tetrahydrofuran

5: 95 percent / CrO₃*H₂SO₄ / acetone / 0 °C

6: 77 percent / LDA / -78 °C

7: HCO₂H / Pd (black) / methanol

8: NEt₃ / dimethylformamide

9: 1.) 1N NaOH, 2.) citric acid / tetrahydrofuran

With chromium(VI) oxide; hydrogenchloride; dmap; sodium hydroxide; sodium tetrahydroborate; formic acid; sulfuric acid; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; citric acid; lithium diisopropyl amide; palladium; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4039(00)73701-4

Reference yield:

: 131150-35-1
(S)-2-(dibenzylamino)-N'-methoxy-N'-methyl-3-phenylpropane amide

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

Guidance literature:: Multi-step reaction with 8 steps

1: 93 percent / tetrahydrofuran / 0 °C

2: NaBH₄ / methanol / 0 °C

3: 92 percent / 3N HCl / tetrahydrofuran

4: 95 percent / CrO₃*H₂SO₄ / acetone / 0 °C

5: 77 percent / LDA / -78 °C

6: HCO₂H / Pd (black) / methanol

7: NEt₃ / dimethylformamide

8: 1.) 1N NaOH, 2.) citric acid / tetrahydrofuran

With chromium(VI) oxide; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; formic acid; sulfuric acid; triethylamine; citric acid; lithium diisopropyl amide; palladium; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4039(00)73701-4