N-(tert-butoxycarbonyl)valine-O-benzyl-L-threonine benzyl ester

Base Information

• Chemical Name: N-(tert-butoxycarbonyl)valine-O-benzyl-L-threonine benzyl ester
• CAS No.: 69541-82-8
• Molecular Formula: C₂₈H₃₈N₂O₆
• Molecular Weight: 498.62
• Mol file: 69541-82-8.mol

Synonyms:N-(tert-butoxycarbonyl)valine-O-benzyl-L-threonine benzyl ester

Chemical Property of N-(tert-butoxycarbonyl)valine-O-benzyl-L-threonine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(tert-butoxycarbonyl)valine-O-benzyl-L-threonine benzyl ester

There total 3 articles about N-(tert-butoxycarbonyl)valine-O-benzyl-L-threonine benzyl 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: 72.0%

(2S,3R)-benzyl 2-amino-3-(benzyloxy)butanoate hydrochloride (67580-86-3) + t-Boc-L-valine (13734-41-3) → N-(tert-butoxycarbonyl)valine-O-benzyl-L-threonine benzyl ester (69541-82-8)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 20h;

DOI:10.1246/bcsj.79.921

Reference yield:

N‐(tert‐butoxycarbonyl)‐O‐benzyl‐L‐threonine benzyl ester (54276-70-9) → N-(tert-butoxycarbonyl)valine-O-benzyl-L-threonine benzyl ester (69541-82-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 985 mg / CF₃COOH / 1 h / 20 °C

2: 72 percent / ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; HOBt / dimethylformamide / 20 h / 20 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In N,N-dimethyl-formamide;

DOI:10.1039/b202298b

Reference yield:

t-Boc-L-valine (13734-41-3) + (2S,3R)-benzyl 2-amino-3-(benzyloxy)butanoate oxalate (42001-91-2) → N-(tert-butoxycarbonyl)valine-O-benzyl-L-threonine benzyl ester (69541-82-8)

Guidance literature:

With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide;

DOI:10.1271/bbb1961.46.1865

upstream raw materials:

t-Boc-L-valine

(2S,3R)-benzyl 2-amino-3-(benzyloxy)butanoate oxalate

(2S,3R)-benzyl 2-amino-3-(benzyloxy)butanoate hydrochloride

N‐(tert‐butoxycarbonyl)‐O‐benzyl‐L‐threonine benzyl ester

Downstream raw materials:

N-[(1,1-dimethylethoxy)carbonyl]-L-valyl-L-threonyl-O-(phenylmethyl)-L-serine (1R,2S)-1-[(1S)-2-[(1,1-dimethylethyl)dimethylsilyl]oxy-1-methylethyl]-2-methylhexadecyl ester

stevastelin B3

(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionic acid (R)-1-((1R,2R,3R)-2-hydroxy-1,3-dimethyl-4-oxo-butyl)-tetradecyl ester

N-[(1,1-dimethylethoxy)carbonyl]-L-valyl-L-threonyl-O-(phenylmethyl)-L-serine (1R)-1-[(1R,2R,3R)-3-carboxy-2-hydroxy-1-methylbutyl]tetradecyl ester