100516-54-9

Basic information

• Product Name: Benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate
• Synonyms: CIVENTICHEM CV-2652;CIVENTICHEM CV-2655;BENZYL (2R,3S)-(-)-6-OXO-2,3-DIPHENYL-4-MORPHOLINECARBOXYLATE;benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholin;Benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholine-carboxylate 98%;(2R,3S)-benzyl 6-oxo-2,3- diphenylmorpholine-4-carboxylate;(5R,6S)-(-)-4-Benzyloxycarbonyl-5,6-diphenyl-2-Morpholinone,98%;(2R,3S)-()-N-Z-6-oxo-2,3-diphenylMorpholine
• CAS NO: 100516-54-9
• Molecular Formula: C₂₄H₂₁NO₄
• Molecular Weight: 387.43
• Product Categories: Chiral Building Blocks;Heterocyclic Building Blocks;Morpholines
• Mol File: 100516-54-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 205-207 °C(lit.)
• Boiling Point: 583.5 °C at 760 mmHg
• Flash Point: 306.7 °C
• Appearance: /Solid
• Density: 1.242g/cm³
• Vapor Pressure: 1.33E-13mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly)
• CAS DataBase Reference: Benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate(100516-54-9)
• EPA Substance Registry System: Benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate(100516-54-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 100516-54-9(Hazardous Substances Data)

Usage

Description

Benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is a chiral compound with a unique molecular structure, featuring a benzyl group, two phenyl groups, and a 6-oxo-2,3-diphenylmorpholine core. It is characterized by its (2R,3S) stereochemistry and exhibits optical activity, making it a valuable intermediate in the synthesis of various pharmaceuticals and biologically active compounds.

Uses

Used in Pharmaceutical Industry:
Benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is used as a key intermediate in the optimized large-scale synthesis of L-m-tyrosine, an essential amino acid with potential therapeutic applications in various medical conditions.
Used in Organic Synthesis:
This chiral compound is also utilized in the asymmetric synthesis of Fmoc-L-cyclopentylglycine, a protected amino acid derivative that is commonly used in peptide synthesis. Its unique stereochemistry allows for the selective formation of desired enantiomers, which is crucial for the development of enantiomerically pure pharmaceuticals and agrochemicals.

InChI:InChI=1/C24H21NO4/c26-21-16-25(24(27)28-17-18-10-4-1-5-11-18)22(19-12-6-2-7-13-19)23(29-21)20-14-8-3-9-15-20/h1-15,22-23H,16-17H2/t22-,23+/m0/s1

Upstream product

• 100516-60-7 (1'S,2'R)-ethyl N-(benzyloxycarbonyl)-N-(1',2'-diphenyl-2'-hydroxyethyl)glycinate 
• 23190-16-1 (1R,2S)-2-Amino-1,2-diphenylethanol 
• 105-36-2 ethyl bromoacetate 
• 501-53-1 benzyl chloroformate 
• 100678-82-8 2-((1S,2R)-2-hydroxy-1,2-diphenylethylamino)acetic acid ethyl ester 
• 530-36-9 2-amino-1,2-diphenylethanol 
• 441-38-3 benzoin oxime 
• 530-36-9 erythro-2-amino-1,2-diphenylethanol 

Downstream Products

• 146346-66-9 (3S,5S,6R)-3-(6-Iodo-hexyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester 
• 146346-65-8 (3S,5S,6R)-3-(5-Iodo-pentyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester 
• 100516-55-0 (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(2'-propenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 
• 144542-63-2 (3S,5S,6R)-3-(3-Chloro-propyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester 
• 144542-64-3 (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(4'-pentenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 
• 135560-80-4 (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(3'-butenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 
• 100570-94-3 (5S,6R)-3-Bromo-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester 
• 111934-06-6 (3S,5S,6R)-4-(benzyloxycarbonyl)-3-bromo-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 
• 136707-25-0 (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-propyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 
• 129274-24-4 (5S,6R)-3-(1-Hydroxy-ethyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester 
• 129274-25-5 (5S,6R)-3-(1-Hydroxy-butyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester 
• 129274-26-6 (5S,6R)-3-(1-Hydroxy-2-methyl-propyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester 
• 145761-32-6 (3S,5S,6R)-4-(Benzyloxycarbonyl)-3-(dimethoxyphosphoryl)-5,6-diphenyl-2,3,5,6-tetrahydro-1,4-oxazin-2-one 
• 100516-58-3 (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-methyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 

Relevant articles and documents

An improved synthesis of optically pure 4-Boc-5,6-diphenylmorpholin-2-one and 4-Cbz-5,6-diphenylmorpholin-2-one

A convenient synthesis of optically pure 4-Boc-5,6-diphenylmorpholin-2-one and 4-Cbz-5,6-diphenylmorpholin-2-one by reaction of (+)- or (-)-2-amino-1,2-diphenylethanol with ethyl bromoacetate, followed by N-protection, and p-TsOH-mediated ring-closure is

An enantioselective synthesis of the Williams glycine template

The Williams glycine template for amino acid synthesis, benzyl (2R,3S)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate (1), was prepared in enantiomerically pure form in six steps from benzaldehyde in 48% overall yield. The initial chirality of the molecule wa

Practical Asymmetric Syntheses of α-Amino Acids through Carbon-Carbon Bond Constructions on Electrophilic Glycine Templates

The optically active D- and L-erythro-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-ones (3) and D- and L-erythro-4-(tert-butoxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-ones (3) can be efficiently brominated to serve as electrophilic glycine templates for the asymmetric synthesis of amino acids.It was found that coupling to these templates can proceed with either net retention or net inversion of stereochemistry.The final deblocking to the amino acids is accomplished with either dissolving-metal reduction or catalytic hydrogenolysis.The syntheses of β-ethyl aspartic acid, norvaline, allylglycine, alanine, norleucine, homophenylalanine, p-methoxyhomophenylalanine, cyclopentylglycine, and cyclopentenylglycine and a formal synthesis of clavalanine are described.In addition, the direct asymmetric syntheses of N-t-BOC-allylglycine and N-t-BOC-cyclopentenylglycine are described.