Benzenepropanethioic acid, a-[[(1,1-dimethylethoxy)carbonyl]amino]-, (S)-

Base Information

• Chemical Name: Benzenepropanethioic acid, a-[[(1,1-dimethylethoxy)carbonyl]amino]-, (S)-
• CAS No.: 81000-39-7
• Molecular Formula: C14H19NO3S
• Molecular Weight: 281.376
• Mol file: 81000-39-7.mol

Synonyms:

Chemical Property of Benzenepropanethioic acid, a-[[(1,1-dimethylethoxy)carbonyl]amino]-, (S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzenepropanethioic acid, a-[[(1,1-dimethylethoxy)carbonyl]amino]-, (S)-

There total 7 articles about Benzenepropanethioic acid, a-[[(1,1-dimethylethoxy)carbonyl]amino]-, (S)- 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: 90.0%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanethioic S-acid (81000-39-7)

Guidance literature:

With hydrogen sulfide; 1,1'-carbonyldiimidazole; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1039/c39930000094

Reference yield:

S-α-methylphenacyl N-tert-butoxycarbonyl-L-thiophenylalainate → (S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanethioic S-acid (81000-39-7)

Guidance literature:

With acetic acid; zinc; In water; at 25 ℃;

DOI:10.1039/c6ob02256a

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine 9-fluorenylmethyl thioester (1330059-29-4) → (S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanethioic S-acid (81000-39-7)

Guidance literature:

N-tert-butoxycarbonyl-L-phenylalanine 9-fluorenylmethyl thioester; With piperidine; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

With hydrogenchloride; In N,N-dimethyl-formamide;

DOI:10.1021/ja2065158

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

(C₅H₉O₂)C₉H₉NO(O)(CO₂C₂H₅)

N-tert-butoxycarbonyl-L-phenylalanine 9-fluorenylmethyl thioester

S-(tert-butyl) (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanethioate

Downstream raw materials:

C₂₂H₂₅NO₄S

N-tert-butoxycarbonyl-L-phenylalanyl-L-alanine ethyl ester

(S)-tert-butyl (1-(4-methylphenylsulfonamido)-1-oxo-3-phenylpropan-2-yl)carbamate

(S)-2-tert-butoxycarbonylamino-3-phenylthiopropionic acid S-benzyl ester

Refernces

• 1、 Mali, Sachitanand M.,Gopi, Hosahudya N.. "Thioacetic acid/NaSH-mediated synthesis of N -protected amino thioacids and their utility in peptide synthesis". . p. 2377 - 2383. Retrieved 2014/04/17.
• 2、 Madhu, Chilakapati,Basavaprabhu,Vishwanatha,Sureshbabu, Vommina V.. "T3P (propylphosphonic anhydride) mediated conversion of N α-protected amino/peptide acids into thioacids". experimental part. p. 1406 - 1409. Retrieved 2012/03/27.