(2R,3R,4S)-4-(tert-butoxycarbonylamino)-3-hydroxy-2-phenylamino-5-phenylpentanoic acid

Base Information

Chemical Name:(2R,3R,4S)-4-(tert-butoxycarbonylamino)-3-hydroxy-2-phenylamino-5-phenylpentanoic acid
CAS No.:930275-65-3
Molecular Formula:C₂₂H₂₈N₂O₅
Molecular Weight:400.475
Hs Code.:

Synonyms:(2R,3R,4S)-4-(tert-butoxycarbonylamino)-3-hydroxy-2-phenylamino-5-phenylpentanoic acid

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Chemical Property of (2R,3R,4S)-4-(tert-butoxycarbonylamino)-3-hydroxy-2-phenylamino-5-phenylpentanoic acid

Chemical Property:

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Technology Process of (2R,3R,4S)-4-(tert-butoxycarbonylamino)-3-hydroxy-2-phenylamino-5-phenylpentanoic acid

There total 7 articles about (2R,3R,4S)-4-(tert-butoxycarbonylamino)-3-hydroxy-2-phenylamino-5-phenylpentanoic 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:

: 930275-64-2
tert-butyl (2S,3R,4R)-4-(ethoxycarbonyl)-3-hydroxy-1-phenyl-4-(phenylamino)butan-2-ylcarbamate

: 930275-65-3
(2R,3R,4S)-4-(tert-butoxycarbonylamino)-3-hydroxy-2-phenylamino-5-phenylpentanoic acid

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; for 10h;
DOI:10.1016/j.bmcl.2006.11.020

Reference yield:

: 13734-34-4
N-tert-butoxycarbonyl-L-phenylalanine

: 930275-65-3
(2R,3R,4S)-4-(tert-butoxycarbonylamino)-3-hydroxy-2-phenylamino-5-phenylpentanoic acid

Guidance literature:: Multi-step reaction with 7 steps

1: NaHCO₃ / dimethylformamide / 5 h / 20 °C

2: CaCl₂; NaBH₄ / ethanol; tetrahydrofuran / 5 h / 0 °C

3: pyridine*SO₃; triethylamine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / 20 °C

4: 89 percent / toluene / 1 h / 80 °C

5: 91 percent / m-CPBA / CH₂Cl₂ / 120 h

6: 60 percent / ethanol / 72 h / 60 °C

7: aq. NaOH / tetrahydrofuran / 10 h

With sodium hydroxide; sodium tetrahydroborate; sulfur trioxide pyridine complex; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium chloride; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 4: Wittig reaction;
DOI:10.1016/j.bmcl.2006.11.020

Reference yield:

: 51987-73-6
(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

: 930275-65-3
(2R,3R,4S)-4-(tert-butoxycarbonylamino)-3-hydroxy-2-phenylamino-5-phenylpentanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: CaCl₂; NaBH₄ / ethanol; tetrahydrofuran / 5 h / 0 °C

2: pyridine*SO₃; triethylamine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / 20 °C

3: 89 percent / toluene / 1 h / 80 °C

4: 91 percent / m-CPBA / CH₂Cl₂ / 120 h

5: 60 percent / ethanol / 72 h / 60 °C

6: aq. NaOH / tetrahydrofuran / 10 h

With sodium hydroxide; sodium tetrahydroborate; sulfur trioxide pyridine complex; triethylamine; 3-chloro-benzenecarboperoxoic acid; calcium chloride; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; toluene; 3: Wittig reaction;
DOI:10.1016/j.bmcl.2006.11.020