112741-50-1

Basic information

• Product Name: tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate
• Synonyms: (2S,3R)-6-Oxo-2,3-diphenyl-morpholine-4-carboxylic acid tert-butyl ester;(5R,6S)-N-Boc-5,6-diphenyl-2-morpholinone;(5S,6R)-(+)-4-Boc-5,6-diphenyl-2-Morpholinone, 99%;(2S,3R)-(+)-N-Boc-6-oxo-2,3-diphenylMorpholine;tert-butyl (2S,3R)-6-oxo-2,3-diphenylMorpholine-4-carboxylate;(2S,3R)-(+)-N-Boc-6-oxo-2,3-diphenylMorpholine;(2S, 3R) - (+) - N- t-butoxycarbonyl-6-oxo-2,3-diphenyl-Morpholine;(2S,3R)-6-Oxo-2,3-diphenyl-4-morpholinecarboxylic Acid 1,1-Dimethylethyl Ester
• CAS NO: 112741-50-1
• Molecular Formula: C₂₁H₂₃NO₄
• Molecular Weight: 353.41
• EINECS: 1312995-182-4
• Product Categories: Chiral Building Blocks;Heterocyclic Building Blocks;Morpholines;API intermediates
• Mol File: 112741-50-1.mol

Chemical Properties

• Melting Point: 206 °C (dec.)(lit.)
• Boiling Point: 509.6 °C at 760 mmHg
• Flash Point: 262 °C
• Appearance: white powder
• Density: 1.175 g/cm³
• Vapor Pressure: 1.67E-10mmHg at 25°C
• Refractive Index: 1.561
• Storage Temp.: 2-8°C
• PKA: -3.28±0.60(Predicted)
• CAS DataBase Reference: tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate(112741-50-1)
• EPA Substance Registry System: tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate(112741-50-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 112741-50-1(Hazardous Substances Data)

Usage

Uses

Used in Asymmetric Synthesis:
tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is used as a chiral auxiliary for the asymmetric synthesis of complex organic molecules, such as cylindrospermopsin and related alkaloids. Its unique stereochemistry and structural features enable the selective formation of desired enantiomers, which is crucial in the development of pharmaceuticals and agrochemicals.
Used in Synthesis of Thrombin Inhibitors:
In the pharmaceutical industry, tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is used as a reactant to synthesize boc-3-(1-methylcyclopropyl)-D-alanine, an intermediate in the preparation of 4-fluoroproline-based analogs. These analogs are potent tripeptide thrombin inhibitors, which have therapeutic applications in the treatment of various blood clot-related disorders.
Used in Total Synthesis of Hepatotoxic Alkaloids:
tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is employed in the total synthesis of potent hepatotoxic alkaloid 7-epicylindrospermopsin. tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is synthesized through a combination of intramolecular 1,3-dipolar cycloaddition and nitroaldol reactions, showcasing the versatility of the chiral auxiliary in complex organic synthesis.
Used in Preparation of Diversely Functionalized Diaminoglutamic Acids:
In the field of amino acid chemistry, tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is used to prepare differentially functionalized diaminoglutamic acids. This is achieved through a radical reaction of selenide with methyl 2-acetamidoacrylate, which can lead to the development of novel bioactive compounds with potential applications in the pharmaceutical industry.

InChI:InChI=1/C21H23NO4/c1-21(2,3)26-20(24)22-14-17(23)25-19(16-12-8-5-9-13-16)18(22)15-10-6-4-7-11-15/h4-13,18-19H,14H2,1-3H3

Upstream product

• 112741-73-8 ethyl (1'R,2'S)-N-tert-butyloxycarbonyl-N-(1',2'-diphenyl-2'-hydroxyethyl)glycinate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 23364-44-5 (1S,2R)-2-Amino-1,2-diphenylethanol 
• 112835-62-8 ethyl (1'R,2'S)-N-(1',2'-diphenyl-2'-hydroxyethyl)glycinate 

Downstream Products

• 282735-66-4 (5R,6S)-5,6-diphenylmorpholin-2-one 
• 681128-21-2 tert-butyl (3R,5R,6S)-3-(2-methylprop-2-enyl)-2-oxo-5,6-diphenylmorpholine-4-carboxylate 
• 120133-42-8 (3SR,5SR,6RS)-4-tert-butoxycarbonyl-5,6-diphenyl-3-(1'-propynyl)-2,3,5,6-tetrahydro-1,4-oxazin-2-one 
• 120133-43-9 (3SR,5SR,6RS)-4-tert-butoxycarbonyl-5,6-diphenyl-3-(1'-pentynyl)-2,3,5,6-tetrahydro-1,4-oxazin-2-one 
• 120133-45-1 (3SR,5SR,6RS)-4-tert-butoxycarbonyl-5,6-diphenyl-3-<((4'-tert-butyldimethylsilyl)oxy)but-1'-yne>-2,3,5,6-tetrahydro-1,4-oxazin-2-one 
• 120133-44-0 (3SR,5SR,6RS)-4-tert-butoxycarbonyl-5,6-diphenyl-3-(1'-octynyl)-2,3,5,6-tetrahydro-1,4-oxazin-2-one 
• 143140-32-3 (3R,5R,6S)-4-tert-butoxycarbonyl-5,6-diphenyl-3-(1-prop-2-enyl)morpholin-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

Diastereoselective intermolecular radical addition to nitrones

The intermolecular radical addition to chiral nitrones 2, 4, 5, and 16 was studied. The isopropyl radical addition to Oppolzer's camphorsultam derivative 2 of glyoxylic nitrone proceeded with excellent diastereoselectivity to give the desired isopropylated product 3a accompanied by the diisopropylated product 3b. A high degree of stereocontrol in the reaction of cyclic nitrone 4 was achieved. The ethyl radical addition to nitrone 4 with triethylborane afforded the desired ethylated product 9a accompanied by the diethylated product 10a and the ethylated nitrone 11a. To evaluate the utility of cyclic nitrone 4, several alkyl radicals were employed in the addition reaction, which afforded the alkylated products 9b-d with excellent diastereoselectivities. In the presence of Mg(ClCO4)2, the ethyl radical addition to BIGN 16 afforded selectively syn isomers. In contrast, the alkyl radical addition to 16 took place even in the absence of Lewis acid to give anti isomers.

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.