121269-56-5

Basic information

• Product Name: (3S,5R)-2,3,5,6-tetrahydro-5-phenyl-3,4-bis(phenylmethyl)-4H-1,4-oxazin-2-one
• Synonyms: (3S,5R)-2,3,5,6-tetrahydro-5-phenyl-3,4-bis(phenylmethyl)-4H-1,4-oxazin-2-one
• CAS NO: 121269-56-5
• Molecular Weight: 357.452
• Mol File: 121269-56-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (3S,5R)-2,3,5,6-tetrahydro-5-phenyl-3,4-bis(phenylmethyl)-4H-1,4-oxazin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,5R)-2,3,5,6-tetrahydro-5-phenyl-3,4-bis(phenylmethyl)-4H-1,4-oxazin-2-one(121269-56-5)
• EPA Substance Registry System: (3S,5R)-2,3,5,6-tetrahydro-5-phenyl-3,4-bis(phenylmethyl)-4H-1,4-oxazin-2-one(121269-56-5)

Safety Data

• Hazardous Substances Data: 121269-56-5(Hazardous Substances Data)

Upstream product

• 121269-45-2 (R)-5-phenyl-3,4,5,6-tetrahydro-2H-1,4-oxazin-2-one 
• 56613-80-0 D-2-phenylglycinol 
• 65085-99-6 (S)-3-benzyl-5-phenyl-3,6-dihydro-[1,4]oxazin-2-one 
• 100-39-0 benzyl bromide 
• 64975-87-7 (3R,5R)-3-benzyl-3,4,5,6-tetrahydro-5-phenyl-2H-1,4-oxazin-2-one 
• 121269-55-4 (5R)-2,3,5,6-tetrahydro-5-phenyl-N-benzyl-4H-1,4-oxazin-2-one 
• 121269-47-4 (3R,5R)-3-benzyl-4-tert-butyloxycarbonyl-5-phenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 

Downstream Products

• 3182-93-2 (L)-phenylalanine ethyl ester hydrochloride 
• 121269-61-2 3-Phenyl-2-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionylamino)-propionic acid ethyl ester 
• 147700-92-3 (3S,5R)-N,3-dibenzyl-3-methyl-5-phenyl-3,4,5,6-tetrahydro-1,4-oxazin-2-one 

Relevant articles and documents

Synthesis of α-Alkyl-α-Benzyl Amino Acid Derivatives, via the Diastereoselective Alkylation of (3S,5R)-N,3-Dibenzyl-3,4,5,6-tetrahydro-5-phenyl-1,4-oxazin-2-one

(3S,5R)-N,3-Dibenzyl-3,4,5,6-tetrahydro-5-phenyl-1,4-oxazin-2-one, derived from L-phenylalanine and phenacyl bromide, was alkylated in a diastereoselective manner to give a range of α-alkylated phenylalanine derivatives.

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.

STEREOSELECTIVE ALKYLATION OF CHIRAL GLYCINE ENOLATE SYNTHONS. THE ENANTIOSELECTIVE SYNTHESIS O α-AMINO ACID DERIVATES

The highly stereoselective alkylation (percentde=99.6 to 97.6) o a new chiral glycine enolate synthon derived from D-2-phenylglycinol is described.Deprotection of the alkylation adducts in a one-pot, three-step procedure provides the ethyl ester hydrochloride salts of the corresponding α-amino acids with no attending racemization.