(S)-2-[(2S,3S,4R)-5-Azido-2-tert-butoxycarbonylamino-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-[(2S,3S,4R)-5-Azido-2-tert-butoxycarbonylamino-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester
• CAS No.: 620960-65-8
• Molecular Formula: C₃₂H₅₅Br₂N₅O₈Si₂
• Molecular Weight: 853.796
• Mol file: 620960-65-8.mol

Synonyms:(S)-2-[(2S,3S,4R)-5-Azido-2-tert-butoxycarbonylamino-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester

Chemical Property of (S)-2-[(2S,3S,4R)-5-Azido-2-tert-butoxycarbonylamino-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[(2S,3S,4R)-5-Azido-2-tert-butoxycarbonylamino-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester

There total 14 articles about (S)-2-[(2S,3S,4R)-5-Azido-2-tert-butoxycarbonylamino-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid 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: 86.0%

3,5-dibromotyrosine methyl ester hydrochloride (61039-29-0) + 5-azido-2-tert-butoxycarbonylamino-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid (620960-64-7) → (S)-2-[(2S,3S,4R)-5-Azido-2-tert-butoxycarbonylamino-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester (620960-65-8)

Guidance literature:

With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2003.08.105

Reference yield:

2-(N-benzyloxycarbonyl)-amino-2-deoxy-3,4-di-(tert-butyl-dimethylsilyloxy)-D-arabino-1,4-lactone (100776-48-5) → (S)-2-[(2S,3S,4R)-5-Azido-2-tert-butoxycarbonylamino-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester (620960-65-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

1.2: 84 percent / NaBH₄ / methanol / 0.5 h / 20 °C

2.1: pyridine / CH₂Cl₂ / 4 h / 20 °C

3.1: 398 mg / 2,6-lutidine / CH₂Cl₂ / 1 h

4.1: H₂ / Pd/C / methanol / 1 h / 20 °C

5.1: 0.77 g / aq. NaHCO₃ / dioxane / 1 h

6.1: 77 percent / PPTS / methanol / 0 °C

7.1: pyridine / 2 h / 0 °C

8.1: 454 mg / NaN₃ / dimethylformamide / 4 h / 80 °C

9.1: 90 percent / DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

10.1: 83 percent / TEMPO; KBr; aq. NaClO / NaHCO₃ / acetone / 3 h

11.1: 85 percent / BOP; Et₃N / dimethylformamide / 0 °C

With pyridine; 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium azide; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; potassium bromide; palladium on activated charcoal; sodium hydrogencarbonate; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/j.tet.2004.04.062

Reference yield:

2,2-dimethyl-propionic acid 5-azido-2-tert-butoxycarbonylamino-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentyl ester (620960-63-6) → (S)-2-[(2S,3S,4R)-5-Azido-2-tert-butoxycarbonylamino-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester (620960-65-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

2: 83 percent / TEMPO; KBr; aq. NaClO / NaHCO₃ / acetone / 3 h

3: 85 percent / BOP; Et₃N / dimethylformamide / 0 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; diisobutylaluminium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; potassium bromide; sodium hydrogencarbonate; In dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/j.tet.2004.04.062

upstream raw materials:

3,5-dibromotyrosine methyl ester hydrochloride

5-azido-2-tert-butoxycarbonylamino-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid

di-tert-butyl dicarbonate

t-butyldimethylsiyl triflate