21948-10-7

Basic information

• Product Name: O-BENZYL-(D)-SERINE BENZYL ESTER
• Synonyms: O-BENZYL-(D)-SERINE BENZYL ESTER;(R)-2-AMINO-3-BENZYLOXY-PROPIONIC ACID BENZYL ESTER;O-Benzyl-(D)-Serine Benzyl Ester HCl;(R)-2-Amino-3-benzyloxy-propionicacidbenzylesterhydrochloride;O-Benzyl-dl-serine benzyl ester hydrochloride;Serine, O-(phenylmethyl)-, phenylmethyl ester, hydrochloride (9CI)
• CAS NO: 21948-10-7
• Molecular Formula: C₁₇H₁₉NO₃*ClH
• Molecular Weight: 285.34
• Mol File: 21948-10-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 438.2°C at 760 mmHg
• Flash Point: 181.5°C
• Appearance: /
• Density: 1.158g/cm³
• Vapor Pressure: 7.06E-08mmHg at 25°C
• Refractive Index: 1.573
• CAS DataBase Reference: O-BENZYL-(D)-SERINE BENZYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: O-BENZYL-(D)-SERINE BENZYL ESTER(21948-10-7)
• EPA Substance Registry System: O-BENZYL-(D)-SERINE BENZYL ESTER(21948-10-7)

Safety Data

• Hazardous Substances Data: 21948-10-7(Hazardous Substances Data)

Usage

General Description

O-Benzyl-(D)-serine benzyl ester is a chemical compound used in the pharmaceutical industry for the synthesis of various drugs and peptides. It is a derivative of the amino acid serine and is a white to off-white crystalline powder. O-BENZYL-(D)-SERINE BENZYL ESTER is commonly used in the production of peptide-based pharmaceuticals due to its ability to protect peptide bonds and increase the stability of the final product. O-Benzyl-(D)-serine benzyl ester is also utilized as a building block in the synthesis of complex pharmaceutical compounds and is generally considered to be safe for use in pharmaceutical applications.

InChI:InChI=1/C17H19NO3/c18-16(13-20-11-14-7-3-1-4-8-14)17(19)21-12-15-9-5-2-6-10-15/h1-10,16H,11-13,18H2/t16-/m0/s1

Upstream product

• 100-51-6 benzyl alcohol 
• 86522-27-2 benzyl 3-benzyloxy-2-chloropropanoate 
• 86522-28-3 benzyl 3-benzyloxy-2-chloropropanimidate 

Relevant articles and documents

AMINO ACIDS; 13. INVESTIGATIONS ON THE SYNTHESIS OF DL-SERINE FROM α-HALOACRYLIC ACID DERIVATIVES

The alkoxide-catalyzed addition of alcohols 2 to α-chloroacrylonitrile (1) at -35 degC gives rise to 3-alkoxy-2-chloropropanenitriles 3; at 0-5 degC with excess 2 alkyl 3-alkoxy-2-chloropropanimidates 4 are obtained.The yields of 3 or 4 decrease with increasing pKa values of the alcohols 2.In the basecatalyzed addition of phenols 5 to 1, a temperature-dependent addition equilibrium is set up in which the position of equilibrium is shifted in favour of the addition products 6 with increasing pKa values of 5.The 3-alkoxy-2-chloropropanoates 8, which are readily accessible by hydrolysis of 4, react smoothly with sodium azide in the presence of a phase transfer catalyst to furnish the 3-alkoxy-2-azidopropanoates 10.Starting from benzyl 2-azido-3-benzyloxy-propanoate (10b), the specific syntheses of DL-serine (14), DL-serine hydrochloride (14*HCl), DL-serine methyl ester hydrochloride (13a*HCl), O-benzyl-DL-serine (12b), and O-benzyl-DL-serine benzyl ester hydrochloride (11b*HCl) are possible by variation of the hydrogenation conditions.