121269-46-3

Usage

Uses

Used in Pharmaceutical Industry:
(5R)-3,4,5,6-TETRAHYDRO-5-PHENYL-N-(BENZYLOXYCARBONYL)-4(H)-1,4-OXAZIN-2-ONE is used as a building block for the synthesis of complex molecules due to its unique structure and functional groups.
Used in Medicinal Chemistry:
(5R)-3,4,5,6-TETRAHYDRO-5-PHENYL-N-(BENZYLOXYCARBONYL)-4(H)-1,4-OXAZIN-2-ONE is used as a target for research and development in medicinal chemistry, as its stereochemical arrangement may determine its biological activity and potential therapeutic applications.

Upstream product

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

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 academic research and scientific papers

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.

An expedient route to the glycine templates (R)- or (S)-N-Cbz-5-phenyl-1,4-oxazin-2-one

An economical and practical route to the title compounds is described. The three step, essentially 'one pot' sequence proceeds in overall yields of up to 80% without the need for chromatography of intermediate isolation.

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.