N-Carbobenzoxy-DL-serine

Base Information

• Chemical Name: N-Carbobenzoxy-DL-serine
• CAS No.: 2768-56-1
• Molecular Formula: C11H13NO5
• Molecular Weight: 239.228
• Hs Code.: 29242990
• European Community (EC) Number: 220-455-0
• NSC Number: 118530,286604,22029
• DSSTox Substance ID: DTXSID301308319
• Mol file: 2768-56-1.mol

Synonyms:2768-56-1;N-Cbz-dl-serine;N-Carbobenzoxy-DL-serine;Z-DL-Ser-OH;N-Carbobenzyloxy-DL-serine;2-(((Benzyloxy)carbonyl)amino)-3-hydroxypropanoic acid;N-Benzyloxycarbonyl-DL-serine;3-hydroxy-2-(phenylmethoxycarbonylamino)propanoic acid;Carbobenzyloxy-d,l-serine;DL-Serine, N-[(phenylmethoxy)carbonyl]-;EINECS 220-455-0;MFCD00063143;Serine, N-carboxy-, N-benzyl ester, DL-;Z-DL-serine;Serine, N-benzyl ester, DL-;2-{[(benzyloxy)carbonyl]amino}-3-hydroxypropanoic acid;N-[(Benzyloxy)carbonyl]serine;MFCD00063144;NSC-286604;carbobenzoxy-d,l-serine;Oprea1_876194;SCHEMBL457686;Z-DL-Ser-OH, 99%;((Benzyloxy)carbonyl)DL-serine;N-[(Benzyloxy)carbonyl]serine #;DTXSID301308319;NSC22029;BBL011575;NSC 22029;NSC-22029;NSC118530;NSC286604;STK290901;AKOS000189553;AKOS016038073;N-[(benzyloxy)carbonyl]-(DL)-serine;AB00253;AB02524;HY-W067360;NSC 118530;NSC-118530;NCGC00331988-01;AS-30070;SY007208;SY020999;AM20060830;CS-0059139;FT-0629946;FT-0633402;FT-0698153;(S)-Z-2-AMINO-3-HYDROXYPROPIONIC ACID;EN300-105675;2-benzyloxycarbonylamino-3-hydroxy-propionic acid;AB00172872-04;A819158;SR-01000513543;SR-01000513543-1;Z193028352

Chemical Property of N-Carbobenzoxy-DL-serine

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 2.56E-10mmHg at 25°C
• Melting Point: 124-126 °C(lit.)
• Refractive Index: 1.4960 (estimate)
• 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.: −20°C
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 239.07937252
• Heavy Atom Count: 17
• Complexity: 263

Purity/Quality:

98%,99%, ^*data from raw suppliers

Z-DL-serine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CO)C(=O)O
• Uses: Z-DL-Serine is a derivative of the primary amino acid serine.

Technology Process of N-Carbobenzoxy-DL-serine

There total 9 articles about N-Carbobenzoxy-DL-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: 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: 84.0%

serin (302-84-1,83245-15-2) + benzyl chloroformate (501-53-1,94274-21-2) → Z-DL-serine (2768-56-1)

Guidance literature:

serin; benzyl chloroformate; With sodium hydrogencarbonate; In water; at 0 - 20 ℃; for 24.75h; Inert atmosphere;

With hydrogenchloride; In water; pH=1;

DOI:10.1021/jm2004305

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → N-benzyloxycarbonyl-L-serine (1145-80-8,2768-56-1,6081-61-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Py / tetrahydrofuran / 2 h / -30 °C

2: 84 percent / Et₃N / H₂O; dioxane / 1 h / Ambient temperature

With pyridine; triethylamine; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1055/s-1990-26777

upstream raw materials:

serin

benzyl chloroformate

water

benzyl alcohol

Downstream raw materials:

C₁₅H₂₂N₂O₅

Z-DL-Ser-HN-NH-CH(CH₃)-C₂H₅

N-(benzyloxycarbonyl)-L-serine ethyl ester

N-(benzyloxycarbonyl)-D-serine

Refernces

• 1、 Allainmat, Monique,L'Haridon, Paul,Toupet, Loic,Plusquellec, Daniel. "A New Highly Chemo- and Regioselective Alkoxycarbonylation of Amino Alcohols and Polyols". . p. 27 - 32. Retrieved 2007/10/02.
• 2、 -. "Composition containing a penem or carbapenem antibiotic". . . Retrieved 2008/06/13.