112741-49-8

Basic information

• Product Name: tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate
• Synonyms: CIVENTICHEM CV-2653;CIVENTICHEM CV-2654;TERT-BUTYL (2R,3S)-(-)-6-OXO-2,3-DIPHENYL-4-MORPHOLINECARBOXYLATE;N-TERT-BUTOXYCARBONYL-(2R,3S)-(-)-6-OXO-2,3-DIPHENYL-4-MORPHOLINE;N-BOC(2R, 3S)-(-)-6-OXO-2,3-DIPHENYL-4-MORPHOLINE CARBOXYLATE;tert-butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morph;TERT-BUTYL (2R,3S)-(-)-6-OXO-2,3-DIPHENY L-4-MORPHOLINECARBOXYLATE, 99% (99% EE);(5S,6R)-N-BoC-5,6-diphenyl-2-morpholinone
• CAS NO: 112741-49-8
• Molecular Formula: C₂₁H₂₃NO₄
• Molecular Weight: 353.41
• Product Categories: API intermediates;Chiral Building Blocks;Heterocyclic Building Blocks;Morpholines
• Mol File: 112741-49-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 206 °C (dec.)(lit.)
• Boiling Point: 509.6 °C at 760 mmHg
• Flash Point: 262 °C
• Appearance: /Solid
• Density: 1.175 g/cm³
• Vapor Pressure: 1.67E-10mmHg at 25°C
• Refractive Index: 1.561
• Storage Temp.: 2-8°C
• Solubility: Acetone (Slightly, Heated, Sonicated), Chloroform (Slightly), DMSO (Slightly, So
• PKA: -3.28±0.60(Predicted)
• CAS DataBase Reference: tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate(112741-49-8)
• EPA Substance Registry System: tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate(112741-49-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 112741-49-8(Hazardous Substances Data)

Usage

Description

Tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is an off-white solid that serves as a crucial reactant in the synthesis of various pharmaceutical compounds. It is characterized by its unique molecular structure, which contributes to its reactivity and utility in the preparation of specific drugs.

Uses

Used in Pharmaceutical Industry:
Tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is used as a key reactant for the preparation of (-)-Jorumycin, (-)-Renieramycin G, 3-epi-Jorumycin, and 3-epi-Renieramycin G. These compounds are significant in the development of new drugs due to their potential therapeutic properties.
Additionally, Tert-Butyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate is used as a reactant in the synthesis of collagen cross-link pyridinolines. Collagen cross-linking is an essential process in the stabilization and strengthening of collagen fibers, which are vital components of connective tissues in the body. This application is particularly relevant in the fields of tissue engineering and regenerative medicine, where the enhancement of collagen's structural integrity is of great importance.

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/t18-,19+/m0/s1

Upstream product

• 112741-70-5 (1'S,2'R)-ethyl N-(tert-butyloxycarbonyl)-N-(1',2'-diphenyl-2'-hydroxyethyl)glycinate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 23190-16-1 (1R,2S)-2-Amino-1,2-diphenylethanol 
• 100678-82-8 2-((1S,2R)-2-hydroxy-1,2-diphenylethylamino)acetic acid ethyl ester 
• 530-36-9 2-amino-1,2-diphenylethanol 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 441-38-3 benzoin oxime 

Downstream Products

• 136707-38-5 (3S,5S,6R)-3-(4-Iodo-butyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester 
• 123098-56-6 (3S,5S,6R)-4-(tert-butyloxycarbonyl)-5,6-diphenyl-3-(3'-methyl-2'-butenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 
• 112741-54-5 (3S,5S,6R)-4-(tert-butyloxycarbonyl)-5,6-diphenyl-3-(1'-prop-2'-enyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 
• 144542-72-3 (3S,5S,6R)-4-(tert-butyloxycarbonyl)-5,6-diphenyl-3-(3'-butenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 
• 123098-57-7 (3S,5S,6R)-4-(tert-butyloxycarbonyl)-5,6-diphenyl-3-(phenylmethyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 
• 120133-42-8 (3S,5S,6R)-4-tert-butoxycarbonyl-5,6-diphenyl-3-(1'-propynyl)-2,3,5,6-tetrahydro-1,4-oxazin-2-one 
• 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 (3S,5S,6R)-4-tert-butoxycarbonyl-5,6-diphenyl-3-(1'-pentynyl)-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 
• 120133-44-0 (3S,5S,6R)-4-tert-butoxycarbonyl-5,6-diphenyl-3-(1'-octynyl)-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 
• 120133-45-1 (3S,5S,6R)-4-tert-butoxycarbonyl-5,6-diphenyl-3-<((4'-tert-butyldimethylsilyl)oxy)but-1'-yne>-2,3,5,6-tetrahydro-1,4-oxazin-2-one 
• 112741-51-2 (3S,5S,6R)-3-bromo-4(tert-butoxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 
• 144538-22-7 (5S,6R)-tetrahydro-5,6-diphenyl-2H-1,4-oxazin-2-one 

Relevant articles and documents

Chiral morphine quinoline compound preparation method and chiral amino acid preparation method of compound

The invention provides chiral morpholine compounds. The structural general formula of the chiral morpholine compounds is as shown in the description. The invention further comprises a preparation method of the chiral morpholine compounds. The chiral morpholine compounds are prepared by using benzoin as a starting material, performing reductive amination, and performing chemical resolution on enantiomers and acid-catalyzed ester condensation reaction. The invention further provides amino acid compounds prepared from the chiral morpholine compounds, and a preparation method and application of the amino acid compounds.

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

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.