Diastereoselective synthesis of glycosyl-α-aminoacids

Bouifraden, S.; Lavergne, Jean‐Pierre; Martinez, Jean; Viallefont, Ph.; Riche, C.

doi:10.1016/s0957-4166(97)00067-0

Cited by 8 publications

(1 citation statement)

References 7 publications

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“…The potential utility of this method for the synthesis of densely functionalized NCAs was also explored. In particular, the synthesis of some illustrative carbon-linked glycoglycines, such as α-aminofuranuronic acid derivatives, was undertaken. To this end, we chose to use the β-lactam 34 , Scheme , prepared in 45% yield by addition of benzyloxyacetyl chloride to the imine 33 and triethylamine, according to the method of Bose .…”

Section: Resultsmentioning

confidence: 99%

Practical Synthesis of α-Amino Acid N-Carboxy Anhydrides of Polyhydroxylated α-Amino Acids from β-Lactam Frameworks. Model Studies toward the Synthesis of Directly Linked Peptidyl Nucleoside Antibiotics

et al. 1998

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A straightforward method for the synthesis of polyhydroxylated alpha-amino acid N-carboxy anhydrides (NCAs) is described as the means by which short peptide segments comprised of a polyhydroxylated chain are easily affordable. The entire sequence lies in the preparation of nonracemic 3-hydroxy beta-lactams through the highly diastereoselective Staudinger reaction of hydroxyketene equivalents with chiral alpha-oxyaldehyde-derived imines, followed by TEMPO radical assisted cycloexpansion to the corresponding NCA and subsequent peptide coupling with alpha-amino acid esters. The method has been applied to the synthesis of short peptide segments derived from carbamoylpolyoxamic acid, some glycoglycines, as well as C(2) symmetric hydroxy amino acids.

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Section: Resultsmentioning

confidence: 99%

Practical Synthesis of α-Amino Acid N-Carboxy Anhydrides of Polyhydroxylated α-Amino Acids from β-Lactam Frameworks. Model Studies toward the Synthesis of Directly Linked Peptidyl Nucleoside Antibiotics

et al. 1998

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ChemInform Abstract: Diastereoselective Synthesis of Glycosyl‐α‐amino Acids.

et al. 1997

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Diastereoselective Synthesis of Glycosyl-α-amino Acids.-Some glycosyl-α-amino acid derivatives such as (IV) and (IX) are prepared via coupling of the sugar (I) with the amino esters (II) and (VII). Interestingly, treatment of (I) with (VII) does not yield the expected condensation product but the spirooxazolidine (VIII). In the presence of BOP/iPr 2 NEt the amino acid derived from the amino ester (IIIa) easily undergoes spirolactonization to the compound (V), which undergoes purely O-acyl ring opening with NH 3 . -(BOUIFRADEN, S.; LAVERGNE, J.-P.; MARTINEZ, J.; VIALLEFONT, P.; RICHE, C.; Tetrahedron: Asymmetry 8 (1997) 6, 949-955; Lab. Chim. Biomol., CNRS, Univ. Montpellier II, F-34095 Montpellier, Fr.; EN)

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