N-Cbz-D-Serine

Base Information

• Chemical Name: N-Cbz-D-Serine
• CAS No.: 6081-61-4
• Molecular Formula: C11H13NO5
• Molecular Weight: 239.228
• Hs Code.: 2924297099
• Mol file: 6081-61-4.mol

Synonyms:N-Carbobenzoxy-D-serine;N-Carbobenzyloxy-D-serine;Serine,N-carboxy-, N-benzyl ester, D- (8CI);(Carbobenzyloxy)-D-serine;N-(Benzyloxycarbonyl)-D-serine;

Chemical Property of N-Cbz-D-Serine

Chemical Property:

• Vapor Pressure: 2.56E-10mmHg at 25°C
• Melting Point: 116-119 °C
• Refractive Index: -6 ° (C=6, AcOH)
• Boiling Point: 487.5 °C at 760 mmHg
• PKA: 3.60±0.10(Predicted)
• Flash Point: 248.6 °C
• PSA: 95.86000
• Density: 1.354 g/cm³
• LogP: 0.74920
• Storage Temp.: Store at RT.
• Solubility.: Acetic Acid (Slightly), DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

Z-D-Ser-OH ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Benzyloxycarbonyl-D-serine is D-serine (S270975) with amine protected from eletrophiles by carboxybenzyl group in organic synthesis. N-Benzyloxycarbonyl-D-serine can be used to synthesize acetamido-methoxypropionamides such as Desacetyl Desmethyl Lacosamide (D288325) which is a potent anticonvulsant.

Technology Process of N-Cbz-D-Serine

There total 8 articles about N-Cbz-D-Serine 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: 96.0%

D-Serine (312-84-5,83245-15-2) + benzyl chloroformate (501-53-1,94274-21-2) → N-(benzyloxycarbonyl)-D-serine (6081-61-4)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; for 12h;

DOI:10.1016/j.tetlet.2014.04.008

Reference yield: 84.0%

5-Methyl-2-thioxo-[1,3,4]thiadiazole-3-carboxylic acid benzyl ester (127867-48-5) + L-serine (56-45-1,302-84-1,312-84-5,6898-95-9,60103-26-6,60103-29-9,83245-15-2) → N-benzyloxycarbonyl-L-serine (1145-80-8,2768-56-1,6081-61-4)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; for 1h; Ambient temperature;

DOI:10.1055/s-1990-26777

Reference yield: 74.0%

N-benzyloxycarbonyl-O-tert-butyl-L-serine tert-butyl ester → N-(benzyloxycarbonyl)-D-serine (6081-61-4)

Guidance literature:

With phosphoric acid; In dichloromethane; at 20 ℃; for 14h;

DOI:10.1021/jo061377b

upstream raw materials:

D-Serine

ethanol

Z-DL-serine

benzyl chloroformate

Downstream raw materials:

N-benzyloxycarbonyl-D-serine benzyloxyamide

N-<(Benzyloxy)carbonyl>-D-serine 2,4-Dinitrophenyl Ester

Z-D-Ser-Ala-OTce

(R)-2-benzyloxycarbonylamino-3-hydroxy-N-(3-methylbenzyl)propionamide

Refernces

• 1、 de Léséleuc, Mylène,Kukor, Andrew,Abbott, Shaun D.,Zacharie, Boulos. "Practical Cleavage of Acetals by Using an Odorless Thiol Immobilized on Silica". . p. 7389 - 7393. Retrieved 2019/12/03.
• 2、 Wang, Shengyang,Sun, Jiansong,Zhang, Qingju,Cao, Xin,Zhao, Yachen,Tang, Gongli,Yu, Biao. "Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers". supporting information. p. 2884 - 2888. Retrieved 2018/02/16.