dimethyl(tert-butoxycarbonyl)-D-glutamate

Base Information

• Chemical Name: dimethyl(tert-butoxycarbonyl)-D-glutamate
• CAS No.: 130622-05-8
• Molecular Formula: C₁₂H₂₁NO₆
• Molecular Weight: 275.302
• Mol file: 130622-05-8.mol

Synonyms:

Chemical Property of dimethyl(tert-butoxycarbonyl)-D-glutamate

Chemical Property:

• Boiling Point: 370.9±32.0 °C(Predicted)
• PKA: 10.86±0.46(Predicted)
• Density: 1.117±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature

Purity/Quality:

98.5% ^*data from raw suppliers

(R)-Dimethyl2-((tert-Butoxycarbonyl)amino)pentanedioate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (R)-Dimethyl 2-((tert-Butoxycarbonyl)amino)pentanedioate is a reagent used in the synthesis of amino(aminopyrimidinyl)indazoles as selective 3-phosphoinositide-dependent kinase-1 inhibitors and antitumor agents.

Technology Process of dimethyl(tert-butoxycarbonyl)-D-glutamate

There total 21 articles about dimethyl(tert-butoxycarbonyl)-D-glutamate 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%

di-tert-butyl dicarbonate (24424-99-5) + L-glutamic dimethyl ester hydrochloride (23150-65-4) → dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate (59279-60-6,130622-05-8,861658-15-3)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1002/anie.201402259

Reference yield: 98.0%

methanol (67-56-1) + L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + di-tert-butyl dicarbonate (24424-99-5) → dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate (59279-60-6,130622-05-8,861658-15-3)

Guidance literature:

methanol; L-glutamic acid; With chloro-trimethyl-silane; at 0 - 20 ℃;

di-tert-butyl dicarbonate; With triethylamine; for 3h;

DOI:10.1002/anie.201803849

Reference yield: 98.0%

(S)-dimethyl 2-(bis(tert-butoxycarbonyl)amino)pentanedioate (206128-03-2) → dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate (59279-60-6,130622-05-8,861658-15-3)

Guidance literature:

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

DOI:10.1021/jo026300b

upstream raw materials:

diazomethane

Boc-Glu

methanol

L-glutamic acid

Downstream raw materials:

(2R,4S)-2-((3aR,6R,7R,7aR)-7-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl)-4-tert-butoxycarbonylamino-pentanedioic acid dimethyl ester

dimethyl (2S)-2-{N-[(tert-butoxy)carbonyl]benzyloxycarbonylamino}pentane-1,5-dioate

methyl (S)-2-N,N-di(tert-butoxycarbonyl)amino-5-oxopentanoate

(3S,5S)-(5-methyl-piperidin-3-yl)-carbamic acid tert-butyl ester

Refernces

• 1、 Chalyavi, Farzaneh,Gilmartin, Philip H.,Schmitz, Andrew J.,Fennie, Michael W.,Tucker, Matthew J.. "Synthesis of 5-Cyano-Tryptophan as a Two-Dimensional Infrared Spectroscopic Reporter of Structure". . p. 7528 - 7532. Retrieved 2018.
• 2、 Matsumura, Yoshihiro,Yuki Satoh, Kimihiro Shirai,Onomura, Osamu,Toshihide, Maki. "New reaction conditions using trifluoroethanol for the E-I Hofmann rearrangement". . p. 2057 - 2060. Retrieved 1999.
• 3、 Padron, Jose M.,Kokotos, George,Martin, Tomas,Markidis, Theodoros,Gibbons, William A.,Martin, Victor S.. "Enantiospecific synthesis of α-amino acid semialdehydes: A key step for the synthesis of unnatural unsaturated and saturated α-amino acids". . p. 3381 - 3394. Retrieved 1998.
• 4、 Dardashti, Rebecca Notis,Kumar, Shailesh,Sternisha, Shawn M.,Reddy, Post Sai,Miller, Brian G.,Metanis, Norman. "Selenolysine: A New Tool for Traceless Isopeptide Bond Formation". . p. 4952 - 4957. Retrieved 2020.
• 5、 Wu, Wenbin,Li, Zheng,Zhou, Guangbiao,Jiang, Sheng. "Total synthesis of argyrins A and e". . p. 2488 - 2491. Retrieved 2011.
• 6、 Ma, Yuying,Shang, Chengyou,Yang, Peng,Li, Linfeng,Zhai, Yangyang,Yin, Zheng,Wang, Binghe,Shang, Luqing. "4-Iminooxazolidin-2-one as a Bioisostere of the Cyanohydrin Moiety: Inhibitors of Enterovirus 71 3C Protease". . p. 10333 - 10339. Retrieved 2018.
• 7、 Sch?del, Nicole,Icik, Esra,Martini, Maike,Altevogt, Luca,Ramming, Isabell,Greulich, Andreas,Baro, Angelika,Bilitewski, Ursula,Laschat, Sabine. "Synthesis of Imidazole and Histidine-Derived Cross-Linkers as Analogues of GOLD and Desmosine". supporting information. p. 2260 - 2268. Retrieved 2021/03/04.
• 8、 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.