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

Base Information

• Chemical Name: (R)-2-[(2-tert-Butoxycarbonylamino-acetyl)-methyl-amino]-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid
• CAS No.: 333354-37-3
• Molecular Formula: C₂₆H₄₃IN₂O₆Si
• Molecular Weight: 634.627
• Mol file: 333354-37-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 15 articles about (R)-2-[(2-tert-Butoxycarbonylamino-acetyl)-methyl-amino]-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid 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:

(R)-2-[(2-tert-Butoxycarbonylamino-acetyl)-methyl-amino]-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid methyl ester (333354-23-7) → (R)-2-[(2-tert-Butoxycarbonylamino-acetyl)-methyl-amino]-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid (333354-37-3)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 1h;

DOI:10.1021/ol0100069

Reference yield:

BOC-glycine (4530-20-5) → (R)-2-[(2-tert-Butoxycarbonylamino-acetyl)-methyl-amino]-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid (333354-37-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / EDC; HOBt / dimethylformamide / 20 h / 23 °C

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

With lithium hydroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1021/ol0100069

Reference yield:

triisopropylsilyl chloride (13154-24-0) → (R)-2-[(2-tert-Butoxycarbonylamino-acetyl)-methyl-amino]-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionic acid (333354-37-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / imidazole / dimethylformamide / 2 h / 23 °C

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

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

4: 90 percent / EDC; HOBt / dimethylformamide / 20 h / 23 °C

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

With 1H-imidazole; lithium hydroxide; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ol0100069

upstream raw materials:

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

BOC-glycine

triisopropylsilyl chloride

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

Downstream raw materials:

Trifluoro-acetic acid (3R,9S,11S,13R,14S,16S)-3-(3-iodo-4-triisopropylsilanyloxy-benzyl)-16-isopropyl-4,9,11,13-tetramethyl-2,5,8-trioxo-1-oxa-4,7-diaza-cyclohexadec-14-yl ester

(3R,9S,11S,13R,14S,16S)-14-Hydroxy-3-(3-iodo-4-triisopropylsilanyloxy-benzyl)-16-isopropyl-4,9,11,13-tetramethyl-1-oxa-4,7-diaza-cyclohexadecane-2,5,8-trione

(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

(2S,4S,6R,7S,9S)-9-[(R)-2-[(2-tert-Butoxycarbonylamino-acetyl)-methyl-amino]-3-(3-iodo-4-triisopropylsilanyloxy-phenyl)-propionyloxy]-7-(tert-butyl-dimethyl-silanyloxy)-2,4,6,10-tetramethyl-undecanoic acid tert-butyl ester