| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348406 | Tetrahedron: Asymmetry | 2007 | 5 Pages |
The highly enantioselective synthesis of (2S)-α-(hydroxymethyl)-glutamic acid 2, a potent metabotropic receptor ligand, was accomplished using the improved Schöllkopf methodology for the construction of quaternary α-amino acids and β-lactams. This was converted to a derivative suitably protected for direct use in Fmoc solid phase peptide synthesis.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
(3S,6R)-3-[(Benzyloxy)methyl]-6-isopropyl-1,4-dimethoxy-3-phenethyl-3,6-dihydropyrazineC25H32N2O3Ee >99%[α]D25=-31.0 (c 1, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (3S,6R)
Methyl (2S)-2-amino-2-[(benzyloxy)methyl]-4-phenylbutanoateC19H23NO3Ee >99%[α]D25=-17.1 (c 1, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (2S)
Methyl (2S)-2-[(acetyloxy)methyl]-2-[(tert-butoxycarbonyl)amino]-4-phenylbutanoateC19H27NO6Ee >99%[α]D25=-9.8 (c 1, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (2S)
(4S)-4-[(Acetyloxy)methyl]-4-[(tert-butoxycarbonyl)amino]-5-methoxy-5-oxopentanoic acidC14H23NO8Ee >99%[α]D25=+2.5 (c 1, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (4S)
(2S)-2-Hydroxymethylglutamic acidC6H11NO5Ee >99%[α]D25=+4.5 (c 1, H2O)Source of chirality: asymmetric synthesisAbsolute configuration: (2S)
(4S)-4-[(tert-Butoxycarbonyl)amino]-4-(hydroxymethyl)-5-methoxy-5-oxopentanoic acidC12H21NO7Ee >99%[α]D25=-22.5 (c 1, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (4S)
5-(tert-Butyl)-1-methyl (2S)-2-[(tert-butoxycarbonyl)amino]-2-(tert-butoxymethyl)pentanedioateC20H37NO7Ee >99%[α]D25=-6.9 (c 1, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (2S)
(2S)-5-(tert-Butoxy)-2-[(tert-butoxycarbonyl)amino]-2-(tert-butoxymethyl)-5-oxopentanoic acidC19H35NO7Ee >99%[α]D25=-3.8 (c 1, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (2S)
(2S)-5-(tert-Butoxy)-2-(tert-butoxymethyl)-2-[(9H-fluoren-9-ylmethoxy)carbonyl]amino-5-oxopentanoic acidC29H37NO7Ee >99%[α]D25=-4.1 (c 1, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (2S)
