methyl (S)-N,N-dimethyl-O-(tert-butyldimethylsilyl)tyrosinate

Base Information

• Chemical Name: methyl (S)-N,N-dimethyl-O-(tert-butyldimethylsilyl)tyrosinate
• CAS No.: 1260499-43-1
• Molecular Formula: C₁₈H₃₁NO₃Si
• Molecular Weight: 337.535
• Mol file: 1260499-43-1.mol

Synonyms:methyl (S)-N,N-dimethyl-O-(tert-butyldimethylsilyl)tyrosinate

Chemical Property of methyl (S)-N,N-dimethyl-O-(tert-butyldimethylsilyl)tyrosinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (S)-N,N-dimethyl-O-(tert-butyldimethylsilyl)tyrosinate

There total 4 articles about methyl (S)-N,N-dimethyl-O-(tert-butyldimethylsilyl)tyrosinate 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: 97.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (S)-methyl 2-(dimethylamino)-3-(4-hydroxyphenyl)propanoate (57746-16-4) → methyl (S)-N,N-dimethyl-O-(tert-butyldimethylsilyl)tyrosinate (1260499-43-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 18h;

DOI:10.1271/bbb.100361

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + methyl (2S)-2-amino-3-{4'-[(tert-butyldimethylsilyl)oxy]phenyl}propanoate (216974-09-3) → methyl (S)-N,N-dimethyl-O-(tert-butyldimethylsilyl)tyrosinate (1260499-43-1)

Guidance literature:

With sodium tris(acetoxy)borohydride; In methanol; water; at 20 ℃; for 18h;

DOI:10.1002/anie.202005891

Reference yield:

L-Tyr-OMe (1080-06-4) → methyl (S)-N,N-dimethyl-O-(tert-butyldimethylsilyl)tyrosinate (1260499-43-1)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen / methanol; water / 3 h

2: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 0 °C

With 1H-imidazole; palladium 10% on activated carbon; hydrogen; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1271/bbb.100361

upstream raw materials:

L-Tyr-OMe

L-tyrosine

tert-butyldimethylsilyl chloride

(S)-methyl 2-(dimethylamino)-3-(4-hydroxyphenyl)propanoate

Downstream raw materials:

(2RS,6E,8R,10R)-1-[4-(tert-butyldimethylsilyloxy)phenyl]-2-(N,N-dimethylamino)-8,10-dimethyldodec-6-en-3-one

(2RS,6E,8R,10R)-2-(N,N-dimethylamino)-1-(4-hydroxyphenyl)-8,10-dimethyldodec-6-en-3-one

(S)-3-[4-(tert-butyldimethylsilyloxy)phenyl]-2-(N,N-dimethylamino)-N-methoxy-N-methylpropanamide

(S)-methyl 2-(dimethylamino)-3-(4-hydroxyphenyl)propanoate