Benzyl N-(Diphenylmethylene)-L-serinate

Base Information

• Chemical Name: Benzyl N-(Diphenylmethylene)-L-serinate
• CAS No.: 145362-72-7
• Molecular Formula: C23H21NO3
• Molecular Weight: 359.41800
• DSSTox Substance ID: DTXSID70446633
• Nikkaji Number: J1.520.198C
• Mol file: 145362-72-7.mol

Synonyms:Benzyl N-(Diphenylmethylene)-L-serinate;145362-72-7;L-Serine, N-(diphenylmethylene)-, phenylmethyl ester;benzyl (2S)-2-(benzhydrylideneamino)-3-hydroxypropanoate;N-(Diphenylmethylene)-L-serine Benzyl Ester;SCHEMBL8620176;DTXSID70446633;AKOS030254320;N-diphenylmethylene-serine benzyl ester;J-008093

Chemical Property of Benzyl N-(Diphenylmethylene)-L-serinate

Chemical Property:

• Vapor Pressure: 2.05E-11mmHg at 25°C
• Melting Point: 78-80 °C
• Boiling Point: 514.6oC at 760 mmHg
• PKA: 13.96±0.10(Predicted)
• Flash Point: 265oC
• PSA: 58.89000
• Density: 1.11g/cm3
• LogP: 3.62830
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform, Dichloromethane
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 359.15214353
• Heavy Atom Count: 27
• Complexity: 452

Purity/Quality:

99.90% ^*data from raw suppliers

BenzylN-(Diphenylmethylene)-L-serinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)C(CO)N=C(C2=CC=CC=C2)C3=CC=CC=C3
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)[C@H](CO)N=C(C2=CC=CC=C2)C3=CC=CC=C3

Technology Process of Benzyl N-(Diphenylmethylene)-L-serinate

There total 3 articles about Benzyl N-(Diphenylmethylene)-L-serinate 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: 85.0%

Benzophenone imine (1013-88-3) + L-serine benzyl ester hydrochloride (60022-62-0,879278-55-4,151651-44-4) → N-diphenylmethylene-L-serine benzyl ester (145362-72-7)

Guidance literature:

In dichloromethane; for 24h; Ambient temperature;

DOI:10.1021/ja00052a022

Reference yield: 85.0%

→ N-diphenylmethylene-L-serine benzyl ester (145362-72-7)

Guidance literature:

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → N-diphenylmethylene-L-serine benzyl ester (145362-72-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: toluene-4-sulfonic acid / benzene / 12 h / Reflux; Dean-Stark apparatus

1.2: 1.5 h / 0 °C

2.1: acetonitrile / 20 °C

With toluene-4-sulfonic acid; In acetonitrile; benzene;

DOI:10.1080/07328303.2010.508295

upstream raw materials:

Benzophenone imine

L-serine benzyl ester hydrochloride

benzyl alcohol

Downstream raw materials:

N-diphenylmethylene-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester

N-diphenylmethylene-O-4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl>-L-serine benzyl ester

N-diphenylmethylene-O-4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl>-L-serine benzyl ester

N-diphenylmethylene-O-4)-3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl>-L-serine benzyl ester

Refernces

• 1、 Mitchell,Pratt,Hruby,Polt. "Solid-phase synthesis of O-linked glycopeptide analogues of enkephalin". . p. 2327 - 2342. Retrieved 2007/10/03.
• 2、 Polt,Szabo,Treiberg,Li,Hruby. "General methods for α- or β-O-Ser/Thr glycosides and glycopeptides. Solid-phase synthesis of O-glycosyl cyclic enkephalin analogues". . p. 10249 - 10258. Retrieved 2007/10/02.