L-Aspartic acid, N-[(phenylmethoxy)carbonyl]-, dimethyl ester

Base Information

• Chemical Name: L-Aspartic acid, N-[(phenylmethoxy)carbonyl]-, dimethyl ester
• CAS No.: 35909-93-4
• Molecular Formula: C14H17NO6
• Molecular Weight: 295.292
• Mol file: 35909-93-4.mol

Synonyms:

Chemical Property of L-Aspartic acid, N-[(phenylmethoxy)carbonyl]-, dimethyl ester

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Aspartic acid, N-[(phenylmethoxy)carbonyl]-, dimethyl ester

There total 20 articles about L-Aspartic acid, N-[(phenylmethoxy)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: 93.0%

dimethyl (2S)-2-{(phenylmethoxy)-N-[benzyloxycarbonyl]carbonylamino}-butane-1,4-dioate (699020-10-5) → dimethyl (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate (35909-93-4)

Guidance literature:

With lithium bromide; In acetonitrile; at 63 ℃;

DOI:10.1021/jo049759+

Reference yield: 90.0%

methanol (67-56-1) + N-Cbz-L-Asp (1152-61-0) → dimethyl (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate (35909-93-4)

Guidance literature:

methanol; With acetyl chloride; at 8 - 10 ℃; for 1h; Inert atmosphere;

N-Cbz-L-Asp; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1080/00397911.2018.1509093

Reference yield: 90.0%

methanol (67-56-1) + L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + benzyl chloroformate (501-53-1,94274-21-2) → dimethyl (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate (35909-93-4)

Guidance literature:

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

benzyl chloroformate; With pyridine; at 20 ℃; for 12h;

DOI:10.1021/jo049759+

upstream raw materials:

diazomethane

N-Cbz-L-Asp

methanol

methyl iodide

Downstream raw materials:

[(1S)-3-hydroxy-1-(hydroxymethyl)propyl]carbamic acid phenylmethyl ester

dimethyl (2S)-2-{(phenylmethoxy)-N-[benzyloxycarbonyl]carbonylamino}-butane-1,4-dioate

(S)-benzyl pyrrolidin-3-ylcarbamate

(S)-1-allyl-3-(benzyloxycarbonylamino)pyrrolidine

Refernces

• 1、 Zhang, Yu,Xia, Bo,Li, Yanyan,Lin, Xianfu,Wu, Qi. "Substrate Engineering in Lipase-Catalyzed Selective Polymerization of d -/ l -Aspartates and Diols to Prepare Helical Chiral Polyester". . p. 918 - 926. Retrieved 2021/02/01.
• 2、 Okitsu, Takashi,Nakahigashi, Hikaru,Sugihara, Ryosuke,Fukuda, Ikki,Tsuji, Saki,In, Yasuko,Wada, Akimori. "Silyl Group-Directed 6-exo-dig Iodocyclization of Homopropargylic Carbamates and Amides". . p. 18638 - 18642. Retrieved 2018/12/04.