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

Base Information

• Chemical Name: (R,E/Z)-tert-butyl 4-((6,7-bis(benzyloxy)-3-((tert-butoxycarbonyl)amino)quinolin-2(1H)-ylidene)amino)-2-hydroxybutanoate
• CAS No.: 1428203-72-8
• Molecular Formula: C₃₆H₄₃N₃O₇
• Molecular Weight: 629.753
• Mol file: 1428203-72-8.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 20 articles about (R,E/Z)-tert-butyl 4-((6,7-bis(benzyloxy)-3-((tert-butoxycarbonyl)amino)quinolin-2(1H)-ylidene)amino)-2-hydroxybutanoate 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:

C8H17NO3 (1427521-88-7) + (S)-tert-butyl (6,7-bis(benzyloxy)-2-thioxo-1,2,3,4-tetrahydroquinolin-3-yl)carbamate (1427521-85-4) → (R,Z)-tert-butyl 4-((6,7-bis(benzyloxy)-3-((tert-butoxycarbonyl)amino)quinolin-2(1H)-ylidene)amino)-2-hydroxybutanoate (1428203-72-8,1428203-73-9) + (R,E)-tert-butyl 4-((6,7-bis(benzyloxy)-3-((tert-butoxycarbonyl)amino)quinolin-2(1H)-ylidene)amino)-2-hydroxybutanoate (1428203-72-8,1428203-73-9)

Guidance literature:

With ethanol; mercury(II) diacetate; In tetrahydrofuran; at 55 ℃; for 18h; Overall yield = 75 %; Overall yield = 2.44 g;

DOI:10.1021/ol400490s

Reference yield:

C8H17NO3 (1427521-88-7) + (S)-tert-butyl (6,7-bis(benzyloxy)-2-thioxo-1,2,3,4-tetrahydroquinolin-3-yl)carbamate (1427521-85-4) → (R,Z)-tert-butyl 4-((6,7-bis(benzyloxy)-3-((tert-butoxycarbonyl)amino)quinolin-2(1H)-ylidene)amino)-2-hydroxybutanoate (1428203-72-8,1428203-73-9) + (R,E)-tert-butyl 4-((6,7-bis(benzyloxy)-3-((tert-butoxycarbonyl)amino)quinolin-2(1H)-ylidene)amino)-2-hydroxybutanoate (1428203-72-8,1428203-73-9)

Guidance literature:

With ethanol; mercury(II) diacetate; In tetrahydrofuran; at 55 ℃; for 18h; Overall yield = 75 %; Overall yield = 2.44 g;

DOI:10.1021/ol400490s

Reference yield:

tert-butyl (2R)-4-{[(benzyloxy)carbonyl]amino}-2-hydroxybutanoate (1427521-87-6) → (R,Z)-tert-butyl 4-((6,7-bis(benzyloxy)-3-((tert-butoxycarbonyl)amino)quinolin-2(1H)-ylidene)amino)-2-hydroxybutanoate (1428203-72-8,1428203-73-9) + (R,E)-tert-butyl 4-((6,7-bis(benzyloxy)-3-((tert-butoxycarbonyl)amino)quinolin-2(1H)-ylidene)amino)-2-hydroxybutanoate (1428203-72-8,1428203-73-9)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 20 °C / Inert atmosphere

2: mercury(II) diacetate; ethanol / tetrahydrofuran / 18 h / 55 °C

With ethanol; palladium 10% on activated carbon; mercury(II) diacetate; hydrogen; In tetrahydrofuran; methanol;

DOI:10.1021/ol400490s

upstream raw materials:

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

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

levodopa

L-DOPA methyl ester

Downstream raw materials:

(S)-tert-butyl 8,9-bis(benzyloxy)-5-((tert-butoxycarbonyl)amino)-2,3-dihydro-1H-pyrimido[1,2-a]quinoline-1-carboxylate