((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-acetic acid tert-butyl ester

Base Information

• Chemical Name: ((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-acetic acid tert-butyl ester
• CAS No.: 1054684-42-2
• Molecular Formula: C₂₁H₃₂N₂O₆
• Molecular Weight: 408.495
• Mol file: 1054684-42-2.mol

Synonyms:((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-acetic acid tert-butyl ester

Chemical Property of ((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-acetic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-acetic acid tert-butyl ester

There total 9 articles about ((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-acetic acid tert-butyl 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:

Glycine tert-butyl ester (6456-74-2) + (2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (62023-65-8,76498-21-0,77171-41-6,82848-28-0,105181-72-4,116661-86-0) → ((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-acetic acid tert-butyl ester (1054684-42-2)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 25 ℃;

DOI:10.1021/jm00054a004

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → ((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-acetic acid tert-butyl ester (1054684-42-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 10N NaOH, Na₂CO₃ / H₂O; tetrahydrofuran / Ambient temperature

2: KHCO₃ / dimethylformamide / 12 h

3: aq. LiOH / methanol; tetrahydrofuran

4: HOBt, N-methylmorpholine, DCC / dimethylformamide / 25 °C

With 4-methyl-morpholine; lithium hydroxide; sodium hydroxide; sodium carbonate; benzotriazol-1-ol; potassium hydrogencarbonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00054a004

Reference yield:

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester (51987-73-6) → ((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-acetic acid tert-butyl ester (1054684-42-2)

Guidance literature:

Multi-step reaction with 7 steps

1: diisobutylaluminium hydride / toluene; hexane / -77 °C

2: sodium metabisulfite / H₂O / 5 h / Ambient temperature

3: 25percent aq. HCl / 12 h / 80 °C

4: 10N NaOH, Na₂CO₃ / H₂O; tetrahydrofuran / Ambient temperature

5: KHCO₃ / dimethylformamide / 12 h

6: aq. LiOH / methanol; tetrahydrofuran

7: HOBt, N-methylmorpholine, DCC / dimethylformamide / 25 °C

With 4-methyl-morpholine; hydrogenchloride; lithium hydroxide; sodium hydroxide; sodium disulfite; diisobutylaluminium hydride; sodium carbonate; benzotriazol-1-ol; potassium hydrogencarbonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; hexane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00054a004

upstream raw materials:

Glycine tert-butyl ester

(2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid

di-tert-butyl dicarbonate

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester