(S)-di-tert-butyl 2,2'-((5-(((benzyloxy)carbonyl)amino)-1-(tert-butoxy)-1-oxopentan-2-yl)azanediyl)diacetate

Base Information

• Chemical Name: (S)-di-tert-butyl 2,2'-((5-(((benzyloxy)carbonyl)amino)-1-(tert-butoxy)-1-oxopentan-2-yl)azanediyl)diacetate
• CAS No.: 1175686-41-5
• Molecular Formula: C₂₉H₄₆N₂O₈
• Molecular Weight: 550.693
• Mol file: 1175686-41-5.mol

Synonyms:(S)-di-tert-butyl 2,2'-((5-(((benzyloxy)carbonyl)amino)-1-(tert-butoxy)-1-oxopentan-2-yl)azanediyl)diacetate

Chemical Property of (S)-di-tert-butyl 2,2'-((5-(((benzyloxy)carbonyl)amino)-1-(tert-butoxy)-1-oxopentan-2-yl)azanediyl)diacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-di-tert-butyl 2,2'-((5-(((benzyloxy)carbonyl)amino)-1-(tert-butoxy)-1-oxopentan-2-yl)azanediyl)diacetate

There total 2 articles about (S)-di-tert-butyl 2,2'-((5-(((benzyloxy)carbonyl)amino)-1-(tert-butoxy)-1-oxopentan-2-yl)azanediyl)diacetate 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: 87.0%

bromoacetic acid tert-butyl ester (5292-43-3) + (S)-2-amino-5-(((benzyloxy)carbonyl)amino)pentanoic acid tert-butyl ester (53054-01-6) → (S)-di-tert-butyl 2,2'-((5-(((benzyloxy)carbonyl)amino)-1-(tert-butoxy)-1-oxopentan-2-yl)azanediyl)diacetate (1175686-41-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 55 ℃; for 24h; Inert atmosphere;

DOI:10.1002/anie.201802746

Reference yield:

N-carboxybenzyl-L-ornithine (3304-51-6,118578-06-6) → (S)-di-tert-butyl 2,2'-((5-(((benzyloxy)carbonyl)amino)-1-(tert-butoxy)-1-oxopentan-2-yl)azanediyl)diacetate (1175686-41-5)

Guidance literature:

Multi-step reaction with 2 steps

1: perchloric acid / 72 h / 20 °C

2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 h / 55 °C / Inert atmosphere

With perchloric acid; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;

DOI:10.1002/anie.201205701 DOI:10.1002/anie.201205701

Reference yield:

(S)-di-tert-butyl 2,2'-((5-(((benzyloxy)carbonyl)amino)-1-(tert-butoxy)-1-oxopentan-2-yl)azanediyl)diacetate (1175686-41-5) → (S)-4-((2-((4-((4-(bis(2-(tert-butoxy)-2-oxoethyl)amino)-5-(tert-butoxy)-5-oxopentyl)amino)-6-(octadecylamino)-1,3,5-triazin-2-yl)amino)ethyl)carbamoyl)-2-(6-(dimethylamino)-3-(dimethyliminio)-3H-xanthen-9-yl)benzoate

Guidance literature:

Multi-step reaction with 4 steps

1.1: 10% Pd/C; hydrogen / ethanol / 72 h / 20 °C / 22502.3 Torr

2.1: collidine / 1,4-dioxane / 1.5 h / 140 °C / Microwave irradiation

3.1: palladium; hydrogen / ethanol / 48 h / 20 °C / 22502.3 Torr

4.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere

4.2: Inert atmosphere; Heating

With 10% Pd/C; hydrogen; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; palladium; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; ethanol; N,N-dimethyl-formamide;

DOI:10.1002/anie.201205701 DOI:10.1002/anie.201205701

upstream raw materials:

bromoacetic acid tert-butyl ester

(S)-2-amino-5-(((benzyloxy)carbonyl)amino)pentanoic acid tert-butyl ester

N-carboxybenzyl-L-ornithine