(R)-4-(((benzyloxy)carbonyl)amino)-1-(tert-butoxy)-1-oxobutan-2-yl 4-nitrobenzoate

Base Information

• Chemical Name: (R)-4-(((benzyloxy)carbonyl)amino)-1-(tert-butoxy)-1-oxobutan-2-yl 4-nitrobenzoate
• CAS No.: 1427521-86-5
• Molecular Formula: C₂₃H₂₆N₂O₈
• Molecular Weight: 458.468
• Mol file: 1427521-86-5.mol

Synonyms:(R)-4-(((benzyloxy)carbonyl)amino)-1-(tert-butoxy)-1-oxobutan-2-yl 4-nitrobenzoate

Chemical Property of (R)-4-(((benzyloxy)carbonyl)amino)-1-(tert-butoxy)-1-oxobutan-2-yl 4-nitrobenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-(((benzyloxy)carbonyl)amino)-1-(tert-butoxy)-1-oxobutan-2-yl 4-nitrobenzoate

There total 3 articles about (R)-4-(((benzyloxy)carbonyl)amino)-1-(tert-butoxy)-1-oxobutan-2-yl 4-nitrobenzoate 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%

4-nitro-benzoic acid (62-23-7) + tert-butyl (2S)-4-{[(benzyloxy)carbonyl]amino}-2-hydroxybutanoate (849773-54-2) → (R)-4-(((benzyloxy)carbonyl)amino)-1-(tert-butoxy)-1-oxobutan-2-yl 4-nitrobenzoate (1427521-86-5)

Guidance literature:

With bis(4-chlorobenzyl) diazene-1,2-dicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 22h;

DOI:10.1021/ol400490s

Reference yield:

S-4-benzyloxycarbonylamino-2-hydroxybutyric acid (40371-50-4) → (R)-4-(((benzyloxy)carbonyl)amino)-1-(tert-butoxy)-1-oxobutan-2-yl 4-nitrobenzoate (1427521-86-5)

Guidance literature:

Multi-step reaction with 2 steps

1: dichloromethane / 20 h / Reflux

2: triphenylphosphine; bis(4-chlorobenzyl) diazene-1,2-dicarboxylate / tetrahydrofuran / 22 h / 20 °C

With bis(4-chlorobenzyl) diazene-1,2-dicarboxylate; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol400490s

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (R)-4-(((benzyloxy)carbonyl)amino)-1-(tert-butoxy)-1-oxobutan-2-yl 4-nitrobenzoate (1427521-86-5)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium carbonate / water; acetone / 20 h / 0 - 5 °C / Inert atmosphere

2: dichloromethane / 20 h / Inert atmosphere; Reflux

3: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 22 h / 20 °C / Inert atmosphere

With di-isopropyl azodicarboxylate; sodium carbonate; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; acetone;

DOI:10.1055/s-0040-1707810

upstream raw materials:

4-nitro-benzoic acid

tert-butyl (2S)-4-{[(benzyloxy)carbonyl]amino}-2-hydroxybutanoate

S-4-benzyloxycarbonylamino-2-hydroxybutyric acid

benzyl chloroformate

Downstream raw materials:

tert-butyl (2R)-4-{[(benzyloxy)carbonyl]amino}-2-hydroxybutanoate

(R,Z)-tert-butyl 4-((6,7-bis(benzyloxy)-3-((tert-butoxycarbonyl)amino)quinolin-2(1H)-ylidene)amino)-2-hydroxybutanoate

(R,E)-tert-butyl 4-((6,7-bis(benzyloxy)-3-((tert-butoxycarbonyl)amino)quinolin-2(1H)-ylidene)amino)-2-hydroxybutanoate