D-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-, dimethyl ester

Base Information

• Chemical Name: D-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-, dimethyl ester
• CAS No.: 130622-08-1
• Molecular Formula: C11H19NO6
• Molecular Weight: 261.275
• Mol file: 130622-08-1.mol

Synonyms:

Chemical Property of D-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-, dimethyl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of D-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-, dimethyl ester

There total 23 articles about D-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-, dimethyl ester 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: 100.0%

methanol (67-56-1) + L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + di-tert-butyl dicarbonate (24424-99-5) → dimethyl N-tert-butoxycarbonyl-L-aspartate (130622-08-1,55747-84-7)

Guidance literature:

methanol; L-Aspartic acid; With chloro-trimethyl-silane; at 0 - 20 ℃; for 25h; Inert atmosphere;

di-tert-butyl dicarbonate; With triethylamine; for 2h; Inert atmosphere;

DOI:10.1016/j.tet.2014.11.059

Reference yield: 99.0%

Boc-Asp-OH (13726-67-5) + methyl iodide (74-88-4) → dimethyl N-tert-butoxycarbonyl-L-aspartate (130622-08-1,55747-84-7)

Guidance literature:

With sodium chloride; potassium carbonate; In water;

Reference yield: 97.0%

dimethyl (2S)-2-{(tert-butoxy)-N-[(tert-butyl)oxycarbonyl]carbonylamino}butanedioate (219617-08-0) → dimethyl N-tert-butoxycarbonyl-L-aspartate (130622-08-1,55747-84-7)

Guidance literature:

With lithium bromide; In acetonitrile; at 65 ℃; for 10h;

DOI:10.1021/jo026300b

upstream raw materials:

diazomethane

(RS)-3-(tert-butoxycarbonylamino)-4-methoxy-4-oxobutanoic acid

di-tert-butyl dicarbonate

dimethyl (R)-2-aminobutanedioate hydrochloride

Downstream raw materials:

(S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester

(3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester

(S)-(-)-methyl 2-[bis(tert-butoxycarbonyl)amino]-4-iodobutanoate

methyl (2S)-2-(tert-butoxycarbonyl)amino-4-iodobutanoate

Refernces

• 1、 Mitchell, Andrew J.,Dunham, Noah P.,Martinie, Ryan J.,Bergman, Jonathan A.,Pollock, Christopher J.,Hu, Kai,Allen, Benjamin D.,Chang, Wei-Chen,Silakov, Alexey,Bollinger, J. Martin,Krebs, Carsten,Boal, Amie K.. "Visualizing the reaction cycle in an Iron(II)- and 2-(Oxo)-glutarate-dependent hydroxylase". . p. 13830 - 13836. Retrieved 2017.
• 2、 Wojewska, Dominika,Kluczyk, Alicja,Slepokura, Katarzyna. "Geometric changes around an N atom due to a urethane-type bis(tert-butoxycarbonyl) substituent". . p. 82 - 86. Retrieved 2013.
• 3、 Reddy, Chada Raji,Reddy, Motatipally Damoder,Dilipkumar, Uredi. "Total synthesis of a pyrrole lactone alkaloid, longanlactone". . p. 6310 - 6313. Retrieved 2014.
• 4、 Becker, Katja,Busker, Sander,Felber, Jan G.,Maier, Martin S.,Poczka, Lena,Scholzen, Karoline,Theisen, Ulrike,Thorn-Seshold, Julia,Thorn-Seshold, Oliver,Zeisel, Lukas,Arnér, Elias S. J.,Brandst?dter, Christina. "Selective, Modular Probes for Thioredoxins Enabled by Rational Tuning of a Unique Disulfide Structure Motif". supporting information. p. 8791 - 8803. Retrieved 2021/06/27.
• 5、 Agelidis, Nektarios,Altevogt, Luca,Baro, Angelika,Bilitewski, Ursula,Bugdayci, Bakiye,Icik, Esra,Jolly, Anthony,L?ffler, Paul,Laschat, Sabine. "Synthesis and Biological Evaluation of a Library of AGE-Related Amino Acid Triazole Crosslinkers". supporting information. . Retrieved 2020/09/01.