(S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester

Base Information

• Chemical Name: (S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester
• CAS No.: 91229-97-9
• Molecular Formula: C₁₇H₂₅NO₅
• Molecular Weight: 323.389
• Mol file: 91229-97-9.mol

Synonyms:(S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester

Chemical Property of (S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester

There total 12 articles about (S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl 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: 98.6%

Boc-Glu-OBn (30924-93-7) → (S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester (91229-97-9)

Guidance literature:

Boc-Glu-OBn; With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -15 ℃; for 0.166667h;

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -15 ℃; for 0.166667h;

DOI:10.1016/j.tet.2005.08.029

Reference yield: 92.0%

benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate (113400-36-5,400626-71-3) → (S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester (91229-97-9)

Guidance literature:

With sodium tetrahydroborate; potassium dihydrogenphosphate; In methanol; water; at 0 ℃; for 1.5h;

DOI:10.1016/S0960-894X(99)00546-6

Reference yield: 85.2%

Boc-Glu-OBzl → (S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester (91229-97-9)

Guidance literature:

Boc-Glu-OBzl; With chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; at -15 - -10 ℃; for 1h;

With sodium tetrahydroborate; In tetrahydrofuran; at 0 - 25 ℃; for 0.833333h;

upstream raw materials:

α-benzyl N^α-(tert-butyloxycarbonyl)-L-glutamate

Boc-Glu(OSu)-OBn

benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

2-tert-butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester

Downstream raw materials:

benzyl 2-(S)-[(tert-butoxycarbonyl)amino]-5-iodopentanoate

phenylmethyl (2S)-5-(3-{(2S)-2-[(3,3-dimethyl-3-silabutyl)oxycarbonyl]-2-[(phenylmethoxy)carbonylamino]ethyl}phenoxy)-2-[(tert-butoxy)carbonylamino]pentanoate

(S)-5-Benzyloxy-2-tert-butoxycarbonylamino-pentanoic acid

Boc-(S)-Phs(Bn)-(S)-Phe-(S)-N-Me-Tyr-OMe