121269-46-3

Basic information

• Product Name: (5R)-3,4,5,6-TETRAHYDRO-5-PHENYL-N-(BENZYLOXYCARBONYL)-4(H)-1,4-OXAZIN-2-ONE
• Synonyms: (5R)-3,4,5,6-TETRAHYDRO-5-PHENYL-N-(BENZYLOXYCARBONYL)-4(H)-1,4-OXAZIN-2-ONE
• CAS NO: 121269-46-3
• Molecular Formula: C₁₈H₁₇NO₄
• Molecular Weight: 311.33
• Mol File: 121269-46-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (5R)-3,4,5,6-TETRAHYDRO-5-PHENYL-N-(BENZYLOXYCARBONYL)-4(H)-1,4-OXAZIN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (5R)-3,4,5,6-TETRAHYDRO-5-PHENYL-N-(BENZYLOXYCARBONYL)-4(H)-1,4-OXAZIN-2-ONE(121269-46-3)
• EPA Substance Registry System: (5R)-3,4,5,6-TETRAHYDRO-5-PHENYL-N-(BENZYLOXYCARBONYL)-4(H)-1,4-OXAZIN-2-ONE(121269-46-3)

Safety Data

• Hazardous Substances Data: 121269-46-3(Hazardous Substances Data)

Usage

General Description

The chemical compound (5R)-3,4,5,6-TETRAHYDRO-5-PHENYL-N-(BENZYLOXYCARBONYL)-4(H)-1,4-OXAZIN-2-ONE is a member of the oxazinone family, containing a phenyl group and a benzyloxycarbonyl moiety. It is a cyclic compound with a tetrahydro-oxazinone ring system, and it is chiral with a specific stereochemistry denoted as 5R. (5R)-3,4,5,6-TETRAHYDRO-5-PHENYL-N-(BENZYLOXYCARBONYL)-4(H)-1,4-OXAZIN-2-ONE may have potential pharmaceutical and medicinal applications due to its structure and functional groups, particularly as a building block for the synthesis of more complex molecules. Additionally, its stereochemical arrangement may determine its biological activity, making it an interesting target for further research and development.

Upstream product

• 121269-45-2 (R)-5-phenyl-3,4,5,6-tetrahydro-2H-1,4-oxazin-2-one 
• 501-53-1 benzyl chloroformate 
• 201018-12-4 [Benzyloxycarbonyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-acetic acid ethyl ester 
• 56613-80-0 D-2-phenylglycinol 

Downstream Products

• 121348-77-4 (3S,5R)-2,3,5,6-tetrahydro-3-(phenylmethyl)-5-phenyl-N-(benzyloxycarbonyl)-4H-1,4-oxazin-2-one 
• 121348-78-5 (3S,5R)-2,3,5,6-tetrahydro-3-methyl-5-phenyl-N-(benzyloxycarbonyl)-4H-1,4-oxazin-2-one 
• 121269-54-3 (3R,5R)-2,3,5,6-tetrahydro-3-((benzyloxycarbonyl)methyl)-5-phenyl-N-(benzyloxycarbonyl)-4H-1,4-oxazin-2-one 
• 121348-82-1 (3S,5R)-2,3,5,6-tetrahydro-3-((benzyloxycarbonyl)methyl)-5-phenyl-N-(benzyloxycarbonyl)-4H-1,4-oxazin-2-one 
• 121269-50-9 (3R,5R)-2,3,5,6-tetrahydro-3-methyl-5-phenyl-N-(benzyloxycarbonyl)-4H-1,4-oxazin-2-one 
• 121269-49-6 (3R,5R)-2,3,5,6-tetrahydro-3-(phenylmethyl)-5-phenyl-N-(benzyloxycarbonyl)-4H-1,4-oxazin-2-one 

Relevant articles and documents

Highly diastereoselective alkylation of the Dellaria oxazinone template with bifunctional electrophiles

This study investigates the efficiency of alkylation of the Dellaria oxazinone glycinate template with sensitive bifunctional electrophiles. In addition to improved access to the template, triflate/halide bifunctional combinations provided good yields (85-93%) of highly diastereoselective alkylation products.

Enantioselective Synthesis of α-Amino Acid Derivatives via the Stereoselective Alkylation of a Homochiral Glycine Enolate Synthon

A new synthetic method for the enantioselective preparation of α-amino acid derivatives is presented.The key step involves the diastereoselective alkylation of the new chiral glycine enolate synthons 7 and 8 providing alkylation adducts with de of > 97.6percent in good yields (73-90percent).The reactivities of the enolates of 7 and 8 were extraordinarily sensitive to the metal counterion and solvent.Experimental conditions are described to maintain high diastereoselectivities in the alkylation step for electrophiles varying from highly reactive (α-haloacetate esters) to less reactive (n-butyl iodide).The alkylation diastereoselectivities were established to be under kinetic control by equilibration experiments on selected alkylation products.A model is presented which hinges on an A(1,3) interaction between the termini of the N4-acyl protecting group and the C5-phenyl group of 7 and 8 which in turn dictates the ?-facial selectivity of the enolate.The model successfully accounts for the observed results and is corroborated by the conformation of an alkylation adduct as revealed by a single-crystal X-ray determination.A simple one-pot, three-step deprotection procedure provides the desired α-amino acid as the ethyl ester hydrochloride salts (60-80percent overall yield) with no attending racemization as determined by conversion of the amino acid esters to the corresponding (+)- or (-)-Mosher amides.