4-allyl 1-[(2R)-2-(benzylamino)-3-methoxy-3-oxopropyl] N-(tert-butoxycarbonyl)-L-aspartate

Base Information

• Chemical Name: 4-allyl 1-[(2R)-2-(benzylamino)-3-methoxy-3-oxopropyl] N-(tert-butoxycarbonyl)-L-aspartate
• CAS No.: 1258937-54-0
• Molecular Formula: C₂₃H₃₂N₂O₈
• Molecular Weight: 464.516
• Mol file: 1258937-54-0.mol

Synonyms:4-allyl 1-[(2R)-2-(benzylamino)-3-methoxy-3-oxopropyl] N-(tert-butoxycarbonyl)-L-aspartate

Chemical Property of 4-allyl 1-[(2R)-2-(benzylamino)-3-methoxy-3-oxopropyl] N-(tert-butoxycarbonyl)-L-aspartate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-allyl 1-[(2R)-2-(benzylamino)-3-methoxy-3-oxopropyl] N-(tert-butoxycarbonyl)-L-aspartate

There total 2 articles about 4-allyl 1-[(2R)-2-(benzylamino)-3-methoxy-3-oxopropyl] N-(tert-butoxycarbonyl)-L-aspartate 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: 72.0%

methyl (2R)-2-(benzylamino)-3-hydroxypropanoate (123639-56-5,131110-76-4,144001-42-3) + N-tert-Butoxycarbonyl-L-asaraginsaeure-α-allylester (88224-27-5) → 4-allyl 1-[(2R)-2-(benzylamino)-3-methoxy-3-oxopropyl] N-(tert-butoxycarbonyl)-L-aspartate (1258937-54-0)

Guidance literature:

methyl (2R)-2-(benzylamino)-3-hydroxypropanoate; With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h; Inert atmosphere;

N-tert-Butoxycarbonyl-L-asaraginsaeure-α-allylester; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 25h; chemoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2010.10.007

Reference yield:

methyl (2R)-2-(benzylamino)-3-hydroxypropanoate (123639-56-5,131110-76-4,144001-42-3) + (S)-4-(allyloxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid (132286-77-2) → 4-allyl 1-[(2R)-2-(benzylamino)-3-methoxy-3-oxopropyl] N-(tert-butoxycarbonyl)-L-aspartate (1258937-54-0)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 6h; Inert atmosphere;

DOI:10.1002/chem.201200457

Reference yield: 100.0%

4-allyl 1-[(2R)-2-(benzylamino)-3-methoxy-3-oxopropyl] N-(tert-butoxycarbonyl)-L-aspartate (1258937-54-0) → (2S)-4-(allyloxy)-1-{[(2R)-2-(benzylammonio)-3-methoxy-3-oxopropyl]oxy}-1,4-dioxobutan-2-aminium bis(trifluoroacetate)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tet.2010.10.007

upstream raw materials:

methyl (2R)-2-(benzylamino)-3-hydroxypropanoate

N-tert-Butoxycarbonyl-L-asaraginsaeure-α-allylester

(S)-4-(allyloxy)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoic acid

Downstream raw materials:

C₁₉H₂₅N₃O₆

allyl [(2S,5R)-4-benzyl-5-(hydroxymethyl)-3,6-dioxopiperazin-2-yl]acetate

allyl [(3R,6S)-4-benzyl-3-(tert-butoxycarbonylaminomethyl)-2,5-dioxopiperazin-6-yl]acetate