3-hydroxy-N,O⁴-dimethyl-N-<3(S)-<(tert-butyldimethylsilyl)oxy>-N-<(tert-butyloxy)carbonyl>-N-methyl-4'-iodo-L-phenylalanyl>-L-tyrosine methyl ester

Base Information

• Chemical Name: 3-hydroxy-N,O⁴-dimethyl-N-<3(S)-<(tert-butyldimethylsilyl)oxy>-N-<(tert-butyloxy)carbonyl>-N-methyl-4'-iodo-L-phenylalanyl>-L-tyrosine methyl ester
• CAS No.: 161634-96-4
• Molecular Formula: C₃₃H₄₉IN₂O₈Si
• Molecular Weight: 756.751
• Mol file: 161634-96-4.mol

Synonyms:3-hydroxy-N,O⁴-dimethyl-N-<3(S)-<(tert-butyldimethylsilyl)oxy>-N-<(tert-butyloxy)carbonyl>-N-methyl-4'-iodo-L-phenylalanyl>-L-tyrosine methyl ester

Chemical Property of 3-hydroxy-N,O⁴-dimethyl-N-<3(S)-<(tert-butyldimethylsilyl)oxy>-N-<(tert-butyloxy)carbonyl>-N-methyl-4'-iodo-L-phenylalanyl>-L-tyrosine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-hydroxy-N,O⁴-dimethyl-N-<3(S)-<(tert-butyldimethylsilyl)oxy>-N-<(tert-butyloxy)carbonyl>-N-methyl-4'-iodo-L-phenylalanyl>-L-tyrosine methyl ester

There total 15 articles about 3-hydroxy-N,O⁴-dimethyl-N-<3(S)-<(tert-butyldimethylsilyl)oxy>-N-<(tert-butyloxy)carbonyl>-N-methyl-4'-iodo-L-phenylalanyl>-L-tyrosine methyl 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: 67.0%

N,O4-dimethyl-L-DOPA methyl ester (135226-85-6) + pentafluorophenyl (2S,3S)-3-<(tert-butyldimethylsilyl)oxy>-2--N-methylamino>-3-(4-iodophenyl)propionate (161634-95-3) → 3-hydroxy-N,O4-dimethyl-N-<3(S)-<(tert-butyldimethylsilyl)oxy>-N-<(tert-butyloxy)carbonyl>-N-methyl-4'-iodo-L-phenylalanyl>-L-tyrosine methyl ester (161634-96-4)

Guidance literature:

In tetrahydrofuran; N,N-dimethyl-formamide; at 70 ℃; for 36h;

DOI:10.1021/ja00098a015

Reference yield: 43.0%

N,O4-dimethyl-L-DOPA methyl ester (135226-85-6) + (2S,3S)-3-<(tert-butyldimethylsilyl)oxy>-2--N-methylamino>-3-(4-iodophenyl)propionic acid (161634-80-6) → 3-hydroxy-N,O4-dimethyl-N-<3(S)-<(tert-butyldimethylsilyl)oxy>-N-<(tert-butyloxy)carbonyl>-N-methyl-4'-iodo-L-phenylalanyl>-L-tyrosine methyl ester (161634-96-4) + (2S,3S)-2-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-3-(4-iodo-phenyl)-propionic acid 2-methoxy-5-((S)-2-methoxycarbonyl-2-methylamino-ethyl)-phenyl ester

Guidance literature:

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 10h;

DOI:10.1021/ja00098a015

Reference yield:

(1S,2R)-1-(4-Iodo-phenyl)-2-methylamino-propane-1,3-diol (161634-84-0) → 3-hydroxy-N,O4-dimethyl-N-<3(S)-<(tert-butyldimethylsilyl)oxy>-N-<(tert-butyloxy)carbonyl>-N-methyl-4'-iodo-L-phenylalanyl>-L-tyrosine methyl ester (161634-96-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 46 percent / O₂ / Pt / acetone; H₂O / 12 h

2: 98 percent / K₂CO₃ / tetrahydrofuran; H₂O / 4 h / 25 °C

3: 94 percent / imidazole / dimethylformamide / 48 h / 25 °C

4: 97 percent / K₂CO₃ / tetrahydrofuran; methanol; H₂O / 1 h / 25 °C

5: 90 percent / EDCI / CH₂Cl₂ / 8 h / 25 °C

6: 67 percent / tetrahydrofuran; dimethylformamide / 36 h / 70 °C

With 1H-imidazole; oxygen; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; platinum; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja00098a015

upstream raw materials:

N,O⁴-dimethyl-L-DOPA methyl ester

(2S,3S)-3-<(tert-butyldimethylsilyl)oxy>-2--N-methylamino>-3-(4-iodophenyl)propionic acid

pentafluorophenyl (2S,3S)-3-<(tert-butyldimethylsilyl)oxy>-2--N-methylamino>-3-(4-iodophenyl)propionate

di-tert-butyl dicarbonate