N-tert-butoxycarbonyl-O-tert-butyldimethylsilyl-(S)-4-hydroxyphenylglycine

Base Information

• Chemical Name: N-tert-butoxycarbonyl-O-tert-butyldimethylsilyl-(S)-4-hydroxyphenylglycine
• CAS No.: 112896-90-9
• Molecular Formula: C₁₉H₃₁NO₅Si
• Molecular Weight: 381.544
• Mol file: 112896-90-9.mol

Synonyms:N-tert-butoxycarbonyl-O-tert-butyldimethylsilyl-(S)-4-hydroxyphenylglycine

Chemical Property of N-tert-butoxycarbonyl-O-tert-butyldimethylsilyl-(S)-4-hydroxyphenylglycine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-tert-butoxycarbonyl-O-tert-butyldimethylsilyl-(S)-4-hydroxyphenylglycine

There total 3 articles about N-tert-butoxycarbonyl-O-tert-butyldimethylsilyl-(S)-4-hydroxyphenylglycine 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%

N-tert-butyloxycarbonyl-L-4-hydroxyphenylglycine (69651-48-5) + tert-butyldimethylsilyl chloride (18162-48-6) → N-tert-butoxycarbonyl-O-tert-butyldimethylsilyl-(S)-4-hydroxyphenylglycine (112896-90-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1021/ja00213a050

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → N-tert-butoxycarbonyl-O-tert-butyldimethylsilyl-(S)-4-hydroxyphenylglycine (112896-90-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / 1N aq. NaOH / dioxane / 2 h / Ambient temperature

2: 77 percent / imidazole / dimethylformamide / 9 h / Ambient temperature

With 1H-imidazole; sodium hydroxide; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.3987/COM-94-S(B)52

Reference yield:

(S)-hydroxyphenylglycine (32462-30-9) → N-tert-butoxycarbonyl-O-tert-butyldimethylsilyl-(S)-4-hydroxyphenylglycine (112896-90-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / 1N aq. NaOH / dioxane / 2 h / Ambient temperature

2: 77 percent / imidazole / dimethylformamide / 9 h / Ambient temperature

With 1H-imidazole; sodium hydroxide; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.3987/COM-94-S(B)52

upstream raw materials:

N-tert-butyloxycarbonyl-L-4-hydroxyphenylglycine

tert-butyldimethylsilyl chloride

di-tert-butyl dicarbonate

(S)-hydroxyphenylglycine

Downstream raw materials:

N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester

N-tert-butyoxycarbonyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester

(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester

N-tert-butoxycarbonyl-(S)-alanyl-N-methyl-2-bromo-(R)-tryptophanyl-O-tert-butyldimethylsilyl-(R)-β-tyrosine tert-butyl ester