(+)-(2S)-N-benzyl-1-(tert-butyldimethylsiloxy)but-3-en-2-amine

Base Information

• Chemical Name: (+)-(2S)-N-benzyl-1-(tert-butyldimethylsiloxy)but-3-en-2-amine
• CAS No.: 1099751-78-6
• Molecular Formula: C₁₇H₂₉NOSi
• Molecular Weight: 291.509
• Mol file: 1099751-78-6.mol

Synonyms:(+)-(2S)-N-benzyl-1-(tert-butyldimethylsiloxy)but-3-en-2-amine

Chemical Property of (+)-(2S)-N-benzyl-1-(tert-butyldimethylsiloxy)but-3-en-2-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2S)-N-benzyl-1-(tert-butyldimethylsiloxy)but-3-en-2-amine

There total 11 articles about (+)-(2S)-N-benzyl-1-(tert-butyldimethylsiloxy)but-3-en-2-amine 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: 78.0%

(S)-N-[1-(tert-butyldimethylsilyloxy)but-3-en-2-yl]benzamide (1332503-93-1) + tert-butyldimethylsilyl chloride (18162-48-6) → (+)-(2S)-N-benzyl-1-(tert-butyldimethylsiloxy)but-3-en-2-amine (1099751-78-6)

Guidance literature:

(S)-N-[1-(tert-butyldimethylsilyloxy)but-3-en-2-yl]benzamide; With lithium aluminium tetrahydride; In tetrahydrofuran; Inert atmosphere; Reflux;

tert-butyldimethylsilyl chloride; With 1H-imidazole; In dichloromethane; for 2h; Inert atmosphere;

DOI:10.1021/jo201341q

Reference yield: 57.0%

(2S)-N-benzyl-1-(tert-butyldimethylsilyloxy)-4-(methylsulfinyl)butan-2-amine (1332503-95-3) → (+)-(2S)-N-benzyl-1-(tert-butyldimethylsiloxy)but-3-en-2-amine (1099751-78-6)

Guidance literature:

With calcium carbonate; In 1,2-dichloro-benzene; for 5h; Reflux; Inert atmosphere;

DOI:10.1021/jo201341q

Reference yield:

(2E)-4-(tert-butyldimethylsiloxy)but-2-enyl methyl carbonate (1099751-57-1) + benzylamine (100-46-9) → (2E)-N-benzyl-4-(tert-butyldimethylsiloxy)but-2-en-1-amine (1099751-95-7) + (+)-(2S)-N-benzyl-1-(tert-butyldimethylsiloxy)but-3-en-2-amine (1099751-78-6)

Guidance literature:

With O,O'-((S)-1,1'-binaphthyl-2,2'-diyl)-N,N'-di-(S,S)-(1-naphthalen-1-yl)-ethyl-phosphoramidite; bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine; triethylamine; In tetrahydrofuran; at 20 ℃; for 2h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1055/s-0028-1083158

upstream raw materials:

(2E)-4-(tert-butyldimethylsiloxy)but-2-enyl methyl carbonate

benzylamine

(S)-N-[1-hydroxy-4-(methylthio)butan-2-yl]benzamide

(S)-N-benzyl-1-(tert-butyldimethylsilyloxy)-4-(methylthio)-butan-2-amine

Downstream raw materials:

(S,E)-4-[benzyl(1-tert-butyldimethylsilyloxybut-3-en-2-yl)-amino]-2-methylbut-2-enyl acetate