methyl N-[(benzyloxy)carbonyl]glycylserinate

Base Information

• Chemical Name: methyl N-[(benzyloxy)carbonyl]glycylserinate
• CAS No.: 10239-27-7
• Molecular Formula: C₁₄H₁₈N₂O₆
• Molecular Weight: 310.307
• Mol file: 10239-27-7.mol

Synonyms:L-Serine,N-[N-[(phenylmethoxy)carbonyl]glycyl]-, methyl ester; Serine,N-(N-carboxyglycyl)-, N-benzyl methyl ester (7CI); Serine,N-(N-carboxyglycyl)-, N-benzyl methyl ester, L- (8CI); NSC 145155

Chemical Property of methyl N-[(benzyloxy)carbonyl]glycylserinate

Chemical Property:

• Vapor Pressure: 1.3E-14mmHg at 25°C
• Boiling Point: 586.7°Cat760mmHg
• Flash Point: 308.7°C
• Density: 1.288g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl N-[(benzyloxy)carbonyl]glycylserinate

There total 9 articles about methyl N-[(benzyloxy)carbonyl]glycylserinate 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: 94.0%

methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride (5680-80-8) + N-(Benzyloxycarbonyl)glycine (1138-80-3) → N-(N-benzyloxycarbonyl-glycyl)-L-serine methyl ester (108849-83-8,10239-27-7)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide;

DOI:10.1021/ja00094a008

Reference yield: 81.0%

(S)-serine methyl ester (2788-84-3) + 2-(((benzyloxy)carbonyl)amino)ethanethioic S-acid (16707-70-3) → N-(N-benzyloxycarbonyl-glycyl)-L-serine methyl ester (108849-83-8,10239-27-7)

Guidance literature:

With isopentyl nitrite; In tetrahydrofuran; at 0 ℃; for 0.0833333h; Darkness;

DOI:10.1021/ol1031393

Reference yield:

(S)-serine methyl ester (2788-84-3) + benzyl (2-azido-2-oxoethyl)carbamate (50622-95-2) → N-(N-benzyloxycarbonyl-glycyl)-L-serine methyl ester (108849-83-8,10239-27-7)

Guidance literature:

With ethyl acetate;

upstream raw materials:

(S)-serine methyl ester

benzyl (2-azido-2-oxoethyl)carbamate

N-(Benzyloxycarbonyl)glycine

methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride

Downstream raw materials:

N-benzyloxycarbonylglycylserine

Z-Gly-Ser-hydrazide

H-Gly-Ser-OMe

Z-Gly-Δ-Ala-OMe

Refernces

• 1、 Kricheldorf, Hans R.. "15N NMR Spectroscopy. 30 - Structure/Shift Relationships of Oligopeptides and Copolypeptides, Including Gramicidin S.". . p. 162 - 177. Retrieved 1981.
• 2、 Kita, Yusuke,Nishii, Yuji,Higuchi, Takafumi,Mashima, Kazushi. "Zinc-catalyzed amide cleavage and esterification of β- hydroxyethylamides". supporting information; body text. p. 5723 - 5726. Retrieved 2012/08/07.
• 3、 Pan, Jia,Devarie-Baez, Nelmi O.,Xian, Ming. "Facile amide formation via S -nitrosothioacids". supporting information; experimental part. p. 1092 - 1094. Retrieved 2011/04/25.