2-tert-butoxycarbonylamino-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionic acid 2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester

Base Information

• Chemical Name: 2-tert-butoxycarbonylamino-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionic acid 2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester
• CAS No.: 259738-70-0
• Molecular Formula: C₃₀H₅₅NO₇Si₂
• Molecular Weight: 597.94
• Mol file: 259738-70-0.mol

Synonyms:2-tert-butoxycarbonylamino-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionic acid 2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester

Chemical Property of 2-tert-butoxycarbonylamino-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionic acid 2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-tert-butoxycarbonylamino-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionic acid 2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester

There total 1 articles about 2-tert-butoxycarbonylamino-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionic acid 2-(tert-butyl-dimethyl-silanyloxy)-ethyl 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: 90.0%

Boc-Tyr-OH (3978-80-1) + 2-(tert-butyldimethylsilyloxy)ethyl bromide (86864-60-0) → 2-tert-butoxycarbonylamino-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionic acid 2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester (259738-70-0)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 70 ℃; for 2h;

DOI:10.7164/antibiotics.52.1146

Reference yield:

2-tert-butoxycarbonylamino-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionic acid 2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester (259738-70-0) + methyl iodide (74-88-4) → 2-(tert-butoxycarbonyl-methyl-amino)-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionic acid 2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 20h;

DOI:10.7164/antibiotics.52.1146

Reference yield:

2-tert-butoxycarbonylamino-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionic acid 2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester (259738-70-0) → (6R,9S,11S)-11-Hydroxy-9-{(S)-3-[4-(2-hydroxy-ethoxy)-phenyl]-2-methylamino-propionyloxy}-6-methyl-tetradecanoic acid

Guidance literature:

Multi-step reaction with 5 steps

1: NaH / tetrahydrofuran / 20 h / 0 - 20 °C

2: LiOH / tetrahydrofuran; methanol; H₂O / 0.5 h / 20 °C

3: TEA / tetrahydrofuran / 20 °C

4: DMAP / toluene / 3 h / 20 °C

5: 95 percent TFA / CH₂Cl₂ / 2 h / 20 °C

With dmap; lithium hydroxide; TEA; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 1: Methylation / 2: Hydrolysis / 3: Acylation / 4: Esterification / 5: desilylation; Boc deprotection; ester cleavage;

DOI:10.7164/antibiotics.52.1146

upstream raw materials:

Boc-Tyr-OH

2-(tert-butyldimethylsilyloxy)ethyl bromide

Downstream raw materials:

2-(tert-butoxycarbonyl-methyl-amino)-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionic acid

(-)-PF₁₁₆₃B

9-(2-(tert-butoxycarbonyl-methyl-amino)-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionyloxy)-6-methyl-tetradecanoic acid tert-butyl ester

9-(2-(tert-butoxycarbonyl-methyl-amino)-3-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl}-propionyloxy)-11-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetradecanoic acid tert-butyl ester