Benzyloxycarbonylserine

Base Information

• Chemical Name: Benzyloxycarbonylserine
• CAS No.: 1145-80-8
• Molecular Formula: C11H13NO5
• Molecular Weight: 239.228
• Hs Code.: 29242990
• European Community (EC) Number: 214-546-4
• UNII: 48KP4476DJ
• DSSTox Substance ID: DTXSID40150750
• Nikkaji Number: J80.200J
• Wikidata: Q72516473
• ChEMBL ID: CHEMBL1222399
• Mol file: 1145-80-8.mol

Synonyms:benzyloxycarbonyl-serine;benzyloxycarbonylserine;Cbz-Ser;Cbz-serine

Chemical Property of Benzyloxycarbonylserine

Chemical Property:

• Appearance/Colour: white to cream powder
• Vapor Pressure: 2.56E-10mmHg at 25°C
• Melting Point: 116-119 °C(lit.)
• Refractive Index: 6.1 ° (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.: −20°C
• Solubility.: Acetic Acid (Sparingly), DMSO
• 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:

99% ^*data from raw suppliers

N-Cbz-L-serine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26

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
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@@H](CO)C(=O)O
• Uses: Building block in peptide synthesis. Starting material for the synthesis of various a-amino acids via the b-lactone Building block in peptide synthesis; Starting material for the synthesis of various α-amino acids via the β-lactone

Technology Process of Benzyloxycarbonylserine

There total 33 articles about Benzyloxycarbonylserine 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%

N-benzyloxycarbonyl-L-serine benzyl ester (21209-51-8) → N-(benzyloxycarbonyl)-L-serine (1145-80-8)

Guidance literature:

With 4-methyl-morpholine; In water; acetonitrile; at 30 ℃; for 96h; under 7500600 Torr;

DOI:10.1021/jo00020a001

Reference yield: 100.0%

L-serin (56-45-1,83245-15-2) + di-tert-butyl dicarbonate (24424-99-5) → N-(benzyloxycarbonyl)-L-serine (1145-80-8)

Guidance literature:

With sodium hydroxide;

DOI:10.1016/S0040-4039(99)01613-5

Reference yield: 95.1%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + L-serin (56-45-1,83245-15-2) → N-(benzyloxycarbonyl)-L-serine (1145-80-8)

Guidance literature:

With sodium carbonate; In acetone; at 30 ℃; for 10h; Temperature;

upstream raw materials:

L-serin

benzyl chloroformate

N-(Benzyloxycarbonyloxy)succinimide

dibenzyl dicarbonate

Downstream raw materials:

N-benzyloxycarbonyl-L-serine methyl ester

N-benzyloxycarbonyl-O-chloroacetyl-L-serine

O-tert-butyl L-serine tert-butyl ester

O-(1,1-dimethylethyl)-N-[(phenylmethoxy)carbonyl]-L-serine 1,1-dimethylethyl ester

Refernces

• 1、 Pehere, Ashok D.,Abell, Andrew D.. "An improved large scale procedure for the preparation of N-Cbz amino acids". . p. 1493 - 1494. Retrieved 2011.
• 2、 Sutherland, Mathew,Li, Alice,Kaghad, Anissa,Panagopoulos, Dimitrios,Li, Fengling,Szewczyk, Magdalena,Smil, David,Scholten, Cora,Bouché, Léa,Stellfeld, Timo,Arrowsmith, Cheryl H.,Barsyte, Dalia,Vedadi, Masoud,Hartung, Ingo V.,Steuber, Holger,Britton, Robert,Santhakumar, Vijayaratnam. "Rational Design and Synthesis of Selective PRMT4 Inhibitors: A New Chemotype for Development of Cancer Therapeutics**". supporting information. p. 1116 - 1125. Retrieved 2021/03/08.
• 3、 -. "Synthesis method and application of 1-aza -5-germanium-5-alkyl bicyclic [3.3.3] undecane compound.". Paragraph 0216; 0221. . Retrieved 2020/05/11.