L-Serine, O-[(1,1-dimethylethyl)dimethylsilyl]-N-[(4-methylphenyl)sulfonyl]-, methyl ester

Base Information

• Chemical Name: L-Serine, O-[(1,1-dimethylethyl)dimethylsilyl]-N-[(4-methylphenyl)sulfonyl]-, methyl ester
• CAS No.: 209266-09-1
• Molecular Formula: C17H29NO5SSi
• Molecular Weight: 387.572
• Mol file: 209266-09-1.mol

Synonyms:

Chemical Property of L-Serine, O-[(1,1-dimethylethyl)dimethylsilyl]-N-[(4-methylphenyl)sulfonyl]-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Serine, O-[(1,1-dimethylethyl)dimethylsilyl]-N-[(4-methylphenyl)sulfonyl]-, methyl ester

There total 6 articles about L-Serine, O-[(1,1-dimethylethyl)dimethylsilyl]-N-[(4-methylphenyl)sulfonyl]-, methyl 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: 100.0%

methyl (2S)-3-hydroxy-2-{[(4-methylphenyl)sulfonyl]amino}propanoate (17136-46-8) + tert-butyldimethylsilyl chloride (18162-48-6) → methyl (S)-3-tret-butyldimethylsilyloxy-2-(4-methylphenylsulfamido)propanoate (209266-09-1)

Guidance literature:

DOI:10.1021/jo962307f

Reference yield: 83.0%

L-2-aminobutyric acid (1492-24-6) + tert-butyldimethylsilyl chloride (18162-48-6) + acetyl chloride (75-36-5) + p-toluenesulfonyl chloride (98-59-9) → methyl (S)-3-tret-butyldimethylsilyloxy-2-(4-methylphenylsulfamido)propanoate (209266-09-1)

Guidance literature:

L-2-aminobutyric acid; acetyl chloride; In methanol; for 16h; Reflux;

p-toluenesulfonyl chloride; With triethylamine; In dichloromethane; at 0 - 20 ℃; for 18h;

tert-butyldimethylsilyl chloride; With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/chem.201500886

Reference yield: 76.0%

R-(-)-serine methyl ester hydrochloride (5874-57-7) + tert-butyldimethylsilyl chloride (18162-48-6) + p-toluenesulfonyl chloride (98-59-9) → methyl (S)-3-tret-butyldimethylsilyloxy-2-(4-methylphenylsulfamido)propanoate (209266-09-1)

Guidance literature:

R-(-)-serine methyl ester hydrochloride; p-toluenesulfonyl chloride; With triethylamine; In dichloromethane; chloroform; at 0 ℃; for 48h;

tert-butyldimethylsilyl chloride; With N,N-dimethyl-formamide; at 0 ℃; for 20h; Further stages.;

DOI:10.1021/ol0170152

upstream raw materials:

methyl (2S)-3-hydroxy-2-{[(4-methylphenyl)sulfonyl]amino}propanoate

tert-butyldimethylsilyl chloride

R-(-)-serine methyl ester hydrochloride

p-toluenesulfonyl chloride

Downstream raw materials:

N-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-4-methyl-benzenesulfonamide

N-Benzyl-N-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxymethyl-ethyl]-4-methyl-benzenesulfonamide

N-Benzyl-N-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-4-methyl-benzenesulfonamide

methyl (S)-3-(tert-butyldimethylsilyloxy)-2-{N-(prop-2-ynyl)-4-toluenesulfonamido}propanoate