benzyl (S)-2-[N-(benzyloxycarbonyl)amino]-5-[N-(tert-butoxy)-N-(2-nitrophenylsulfonyl)amino]pentanoate

Base Information

• Chemical Name: benzyl (S)-2-[N-(benzyloxycarbonyl)amino]-5-[N-(tert-butoxy)-N-(2-nitrophenylsulfonyl)amino]pentanoate
• CAS No.: 1373233-95-4
• Molecular Formula: C₃₀H₃₅N₃O₉S
• Molecular Weight: 613.689
• Mol file: 1373233-95-4.mol

Synonyms:benzyl (S)-2-[N-(benzyloxycarbonyl)amino]-5-[N-(tert-butoxy)-N-(2-nitrophenylsulfonyl)amino]pentanoate

Chemical Property of benzyl (S)-2-[N-(benzyloxycarbonyl)amino]-5-[N-(tert-butoxy)-N-(2-nitrophenylsulfonyl)amino]pentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (S)-2-[N-(benzyloxycarbonyl)amino]-5-[N-(tert-butoxy)-N-(2-nitrophenylsulfonyl)amino]pentanoate

There total 5 articles about benzyl (S)-2-[N-(benzyloxycarbonyl)amino]-5-[N-(tert-butoxy)-N-(2-nitrophenylsulfonyl)amino]pentanoate 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:

benzyl L-<(2-benzyloxycarbonyl)amino>-5-hydroxypentanoate (167319-89-3) + O-(1,1-Dimethylethyl)-N-(2-nitrophenylsulfonyl)hydroxylamine → benzyl (S)-2-[N-(benzyloxycarbonyl)amino]-5-[N-(tert-butoxy)-N-(2-nitrophenylsulfonyl)amino]pentanoate (1373233-95-4)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.bmc.2012.02.033

Reference yield:

Cbz-(L)-Glu-OBn (3705-42-8) → benzyl (S)-2-[N-(benzyloxycarbonyl)amino]-5-[N-(tert-butoxy)-N-(2-nitrophenylsulfonyl)amino]pentanoate (1373233-95-4)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / tetrahydrofuran / 1 h / -10 °C

2: sodium tetrahydroborate / water / 5 h / 20 °C

3: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 2 h / 0 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; water; toluene; 3: Mitsunobu reaction;

DOI:10.1016/j.bmc.2012.02.033

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → benzyl (S)-2-[N-(benzyloxycarbonyl)amino]-5-[N-(tert-butoxy)-N-(2-nitrophenylsulfonyl)amino]pentanoate (1373233-95-4)

Guidance literature:

Multi-step reaction with 5 steps

1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 °C

2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

3: triethylamine / tetrahydrofuran / 1 h / -10 °C

4: sodium tetrahydroborate / water / 5 h / 20 °C

5: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 2 h / 0 - 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water; toluene; 5: Mitsunobu reaction;

DOI:10.1016/j.bmc.2012.02.033

upstream raw materials:

Cbz-(L)-Glu-OBn

(S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-benzyl ester 5-tert-butyl ester

benzyl L-<(2-benzyloxycarbonyl)amino>-5-hydroxypentanoate

benzyl alcohol

Downstream raw materials:

benzyl (S)-2-[N-(benzyloxycarbonyl)amino]-5-[N-(tert-butoxy)amino]pentanoate