2-tert-butoxycarbonylamino-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid methyl ester

Base Information

• Chemical Name: 2-tert-butoxycarbonylamino-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid methyl ester
• CAS No.: 333354-35-1
• Molecular Formula: C₂₄H₄₀INO₅Si
• Molecular Weight: 577.575
• Mol file: 333354-35-1.mol

Synonyms:2-tert-butoxycarbonylamino-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid methyl ester

Chemical Property of 2-tert-butoxycarbonylamino-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-tert-butoxycarbonylamino-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid methyl ester

There total 1 articles about 2-tert-butoxycarbonylamino-3-(3-iodo-4-triisopropylsilanyloxy-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: 98.0%

triisopropylsilyl chloride (13154-24-0) + methyl (R)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoate (119336-08-2) → 2-tert-butoxycarbonylamino-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid methyl ester (333354-35-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 23 ℃; for 2h;

DOI:10.1021/ol0100069

Reference yield:

2-tert-butoxycarbonylamino-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid methyl ester (333354-35-1) + methyl iodide (74-88-4) → 2-(tert-butoxycarbonyl-methyl-amino)-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid methyl ester (333354-22-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 60 ℃; for 20h;

DOI:10.1021/ol0100069

Reference yield:

2-tert-butoxycarbonylamino-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid methyl ester (333354-35-1) → (3R,9S,11S,13R,14S,16S)-14-hydroxy-3-[(4-hydroxy-3-iodophenyl)methyl]-4,9,11,13-tetramethyl-16-(propan-2-yl)-1-oxa-4,7-diazacyclohexadecane-2,5,8-trione (156953-84-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaH / dimethylformamide; tetrahydrofuran / 20 h / 60 °C

2.1: 1.22 g / TFA / CH₂Cl₂ / 3 h / 23 °C

3.1: 90 percent / EDC; HOBt / dimethylformamide / 20 h / 23 °C

4.1: LiOH / H₂O; tetrahydrofuran / 1 h / 0 °C

5.1: 98 percent / DCC; DMAP / CH₂Cl₂ / 20 h / -20 °C

6.1: CH₂Cl₂ / 0 - 23 °C

7.1: TFA / CH₂Cl₂ / 3 h / 0 - 23 °C

7.2: 82 percent / BOP; DMAP / CH₂Cl₂ / 24 h / 0 - 23 °C

8.1: 98 percent / TBAF / tetrahydrofuran / 0.25 h / 0 °C

With dmap; lithium hydroxide; tetrabutyl ammonium fluoride; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ol0100069

upstream raw materials:

triisopropylsilyl chloride

methyl (R)-2-((tert-butoxycarbonyl)amino)-3-(4-hydroxy-3-iodophenyl)propanoate

Downstream raw materials:

2-(tert-butoxycarbonyl-methyl-amino)-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid methyl ester

(3R,9S,11S,13R,14S,16S)-14-hydroxy-3-[(4-hydroxy-3-iodophenyl)methyl]-4,9,11,13-tetramethyl-16-(propan-2-yl)-1-oxa-4,7-diazacyclohexadecane-2,5,8-trione

(R)-3-(3-Iodo-4-triisopropylsilanyloxy-phenyl)-2-methylamino-propionic acid methyl ester

(R)-2-[(2-tert-Butoxycarbonylamino-acetyl)-methyl-amino]-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid methyl ester