2-benzyloxycarbonylamino-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid tert-butyl ester

Base Information

• Chemical Name: 2-benzyloxycarbonylamino-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid tert-butyl ester
• CAS No.: 862368-89-6
• Molecular Formula: C₂₇H₃₉NO₅Si
• Molecular Weight: 485.696
• Mol file: 862368-89-6.mol

Synonyms:2-benzyloxycarbonylamino-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid tert-butyl ester

Chemical Property of 2-benzyloxycarbonylamino-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-benzyloxycarbonylamino-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid tert-butyl ester

There total 4 articles about 2-benzyloxycarbonylamino-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid tert-butyl 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: 70.0%

tert-Butyl 2,2,2-trichloroacetimidate (98946-18-0) + (S)-2-(((benzyloxy)carbonyl)amino)-3-(4-((tert-butyldimethylsilyl)oxy)phenyl)propanoic acid (146346-85-2) → 2-benzyloxycarbonylamino-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid tert-butyl ester (862368-89-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1016/j.tetlet.2005.05.060

Reference yield:

Z-L-Tyr-OH (1164-16-5) → 2-benzyloxycarbonylamino-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid tert-butyl ester (862368-89-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / imidazole; DMAP / dimethylformamide

2: 70 percent / BF₃*Et₂O / CH₂Cl₂

With 1H-imidazole; dmap; boron trifluoride diethyl etherate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2005.05.060

Reference yield:

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → 2-benzyloxycarbonylamino-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid tert-butyl ester (862368-89-6)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. NaOH / dioxane

2: 100 percent / imidazole; DMAP / dimethylformamide

3: 70 percent / BF₃*Et₂O / CH₂Cl₂

With 1H-imidazole; dmap; sodium hydroxide; boron trifluoride diethyl etherate; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2005.05.060

upstream raw materials:

tert-Butyl 2,2,2-trichloroacetimidate

(S)-2-(((benzyloxy)carbonyl)amino)-3-(4-((tert-butyldimethylsilyl)oxy)phenyl)propanoic acid

Z-L-Tyr-OH

L-tyrosine

Downstream raw materials:

3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3-hydroxy-2-(2-nitro-benzenesulfonylamino)-propionic acid tert-butyl ester

3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3-fluoro-2-(2-nitro-benzenesulfonylamino)-propionic acid tert-butyl ester

3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-2-(2-nitro-benzenesulfonylamino)-propionic acid tert-butyl ester

(Z)-3-(4-Hydroxy-phenyl)-2-((3S,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-3,4,5,6-tetrahydro-pyridin-2-ylamino)-acrylic acid tert-butyl ester