Z-Ser-obzl

Base Information

• Chemical Name: Z-Ser-obzl
• CAS No.: 21209-51-8
• Molecular Formula: C18H19NO5
• Molecular Weight: 329.353
• Hs Code.: 29242100
• DSSTox Substance ID: DTXSID40426341
• Nikkaji Number: J427.127K
• Wikidata: Q72442125
• Mol file: 21209-51-8.mol

Synonyms:Z-SER-OBZL;21209-51-8;N-Cbz-L-serine benzyl ester;N-Z-L-Serine benzyl ester;benzyl (2S)-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoate;MFCD00037824;N-Carbobenzoxy-L-serine Benzyl Ester;Serine, N-[(phenylmethoxy)carbonyl]-, phenylmethyl ester;Benzyl ((benzyloxy)carbonyl)-L-serinate;Benzyl N-[(benzyloxy)carbonyl]-L-serinate;Z-L-serine benzyl ester;N-(Benzyloxycarbonyl)-L-serine benzyl ester;SCHEMBL2677964;DTXSID40426341;N-Z-L-Serine benzyl ester, 97%;AKOS015889964;AKOS015924163;AM82231;N-(Benzyloxycarbonyl)serine benzyl ester;DS-15090;N-Benzyloxycarbonyl-L-serine benzyl ester;C2873;CS-0037004;C-2300;F10758;EN300-6479749;A815199;J-300246;Benzyl (2S)-2-benzyloxycarbonylamino-3-hydroxypropanoate;(S)-benzyl 2-(benzyloxycarbonylamino)-3-hydroxypropanoate;Benzyl (2S)-2-benzyloxycarbonylamino-3-hydroxy-propanoate;benzyl (2S)-2-(benzyloxycarbonylamino)-3-hydroxy-propanoate;BENZYL (2S)-2-{[(BENZYLOXY)CARBONYL]AMINO}-3-HYDROXYPROPANOATE

Chemical Property of Z-Ser-obzl

Chemical Property:

• Vapor Pressure: 2.97E-12mmHg at 25°C
• Melting Point: 83-86 °C(lit.)
• Refractive Index: 1.58
• Boiling Point: 534.472 °C at 760 mmHg
• PKA: 10.46±0.46(Predicted)
• Flash Point: 277.039 °C
• PSA: 84.86000
• Density: 1.254 g/cm³
• LogP: 2.40800
• Storage Temp.: Store at RT.
• Solubility.: Chloroform, Methanol
• Water Solubility.: Slightly soluble in water.
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 329.12632271
• Heavy Atom Count: 24
• Complexity: 389

Purity/Quality:

95% ^*data from raw suppliers

Z-L-serine benzyl ester ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)C(CO)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)[C@H](CO)NC(=O)OCC2=CC=CC=C2
• Uses: N-Benzyloxycarbonyl-L-serine benzyl ester is used as a building block in peptide synthesis and as a biochemical reagent. It is also used to synthesize the corresponding N-benzyloxycarbonyl-O-tert-butyl-(lor dl)-serine benzyl ester. Further, it serves as a pharmaceutical intermediate.

Technology Process of Z-Ser-obzl

There total 10 articles about Z-Ser-obzl 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: 98.0%

N-(benzyloxycarbonyl)-L-serine (1145-80-8) + benzyl bromide (100-39-0) → N-benzyloxycarbonyl-L-serine benzyl ester (21209-51-8)

Guidance literature:

N-(benzyloxycarbonyl)-L-serine; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; at 80 ℃; for 2h; Inert atmosphere; Schlenk technique;

benzyl bromide; In benzene; for 2h; Inert atmosphere; Schlenk technique;

DOI:10.1002/ejoc.201900143

Reference yield: 92.0%

L-serine benzyl ester p-toluenesulfonate hydrochoride (1738-80-3) + benzyl chloroformate (501-53-1,94274-21-2) → N-benzyloxycarbonyl-L-serine benzyl ester (21209-51-8)

Guidance literature:

With sodium hydrogencarbonate; In water; for 2h; Ambient temperature;

DOI:10.1248/cpb.41.252

Reference yield: 87.0%

N-(benzyloxycarbonyl)-L-serine (1145-80-8) + O-benzyl-N,N'-diisopropylisourea (2978-10-1) → N-benzyloxycarbonyl-L-serine benzyl ester (21209-51-8)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 25.5h;

DOI:10.1039/b004677i

upstream raw materials:

N-(benzyloxycarbonyl)-L-serine

toluene-4-sulfonic acid

benzyl alcohol

benzyl bromide

Downstream raw materials:

N-benzyloxycarbonyl-O-carbamoyl-L-serine benzyl ester

N-benzyloxycarbonyl-O-[bis-(2-chloro-ethyl)-carbamoyl]-L-serine benzyl ester

L-serine ethanolamine phosphate

O,O'-hydroxyphosphoryl-di-L-serine

Refernces

• 1、 Krumb, Matthias,Lucas, Tobias,Opatz, Till. "Visible Light Enables Aerobic Iodine Catalyzed Glycosylation". supporting information. p. 4517 - 4521. Retrieved 2019/08/06.
• 2、 Guanti, Giuseppe,Banfi,Basso,Bondanza,Guglieri,Powles,Riva. "Optimized synthesis of phosphatidylserine". experimental part. p. 367 - 373. Retrieved 2010/12/18.