cas 100516-54-9, Benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate | Articles data ｜lookchem

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100516-54-9

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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
Dastlik, Kim A.,Sundermeier, Uta,Johns, Deidre M.,Chen, Yuyin,Williams, Robert M.
p. 693 - 696
(2005)
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Electrophilic Glycinates: New and Versatile Templates for Asymmetric Amino Acid Synthesis
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Sinclair, Peter J.,Zhai, Dongguan,Reibenspies, Joseph,Williams, Robert M.
p. 1103 - 1104
(1986)
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An enantioselective synthesis of the Williams glycine template
The Williams glycine template for amino acid synthesis, benzyl (2R,3S)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate (1), was prepared in enantiomerically pure form in six steps from benzaldehyde in 48% overall yield. The initial chirality of the molecule wa
Van Den Nieuwendijk,Warmerdam,Brussee,Van Der Gen
p. 801 - 806
(2007/10/02)

Chiral Synthesis of L-γ-Carboxylgutamic Acid (L-Gla)
A two step synthesis involving the use of a chiral template, benzyl (2R,3S)-(-)-6-oxo-2,3-diphenyl-4-morpholine-carboxylate (5a), provides orthogonally protected L-Gla (9) in 60percent overall yield (>99percent ee), with no resolution required.
Schuerman, Marla A.,Keverline, Kathryn I.,Hiskey, Richard G.
p. 825 - 828
(2007/10/02)

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.
Williams, Robert M.,Sinclair, Peter J.,Zhai, Dongguan,Chen, Daimo
p. 1547 - 1557
(2007/10/02)

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Chemical Properties

Melting Point: 205-207 °C(lit.)
Boiling Point: 583.5 °C at 760 mmHg
Flash Point:306.7 °C
Density: 1.242g/cm³
Solubility:Chloroform (Slightly), Dichloromethane (Slightly), DMSO (Slightly)
Storage Temp.:2-8°C
Vapor Pressure: 1.33E-13mmHg at 25°C
Refractive Index: 1.609
PSA: 55.84000
LogP: 4.60250

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