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

Uses

(2R,3S)-(?)-N-Z-6-Oxo-2,3-diphenylmorpholine can be used in the optimized large scale synthesis of L-m-tyrosine. Also used in the asymmetric synthesis of Fmoc-L-cyclopentylglycine.

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

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

Downstream Products

• 146346-66-9 (3S,5S,6R)-3-(6-Iodo-hexyl)-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 
• 222843-51-8 benzyl (2R,3S)-3-<4-(tert-butoxycarbonylmethyl)phenyl>-2-oxo-5,6-diphenyl-morpholine-4-carboxylate 
• 222843-57-4 benzyl (2R,3S)-3-<4-(tert-butoxycarbonyl-difluoro-methyl)phenyl>-2-oxo-5,6-diphenyl-morpholine-4-carboxylate 
• 331251-94-6 (3R,5R,6S)-3-((R)-3-Benzyloxycarbonylamino-1-hydroxy-propyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester 
• 331251-93-5 (3S,5S,6R)-3-((S)-3-Benzyloxycarbonylamino-1-hydroxy-propyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester 
• 351020-28-5 (3S,5S,6R)-3-[1-Benzylamino-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester 
• 863719-47-5 diethyl 2-[4-({(3S,5S,6R)-2-oxo-diphenyl-4-[benzyloxycarbonyl]morpholin-3-yl}methyl)phenyl]propane-1,3-dioate 
• 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 
• 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 
• 144542-63-2 (3S,5S,6R)-3-(3-Chloro-propyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester 

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

Chiral Synthesis of L-γ-Carboxylgutamic Acid (L-Gla)

A two step synthesis involving the use of a chiral template, benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholine-carboxylate (5a), provides orthogonally protected L-Gla (9) in 60percent overall yield (>99percent ee), with no resolution required.

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.