Darstellung und Acylierungen von 1.1‐Dialkyl‐3‐hydroxyharnstoffen

Zinner, G.; Isensee, G.

doi:10.1002/ardp.19743070104

Cited by 10 publications

(1 citation statement)

References 11 publications

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“…After evaporation of the solvents, the oily residue was recrystalliLed (AcOEt/EtOH 95 :5): a colourless compound (4.5 g, 58%), m.p. 111-112" ( [40]: 107-109").…”

Section: Experimental Partmentioning

confidence: 99%

Syntheses of Diamino‐dideoxylyxose Derivatives using Acylnitroso Dienophiles

Defoin

Fritz

Schmidlin

et al. 1987

Helvetica Chimica Acta

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N-Acylnitroso derivatives 6 which were prepared by in-situ oxidation of the corresponding hydroxamic acids 5 reacted instantaneously and in high yields with dihydropyridine 4. The Diels-Alder adducts 8 were formed rcgiospecifically with the acylnitroso dienophiles 6a<, whereas the dienophiles 6d f gave mixtures of both regioisomers 7 and 8. These and some other results [2] were best explained by the FMO theory. The Diels-Alder adducts 7 and 8 gave the corresponding 'unti'-&-glycols when reacted with Os04/N-methylmorpholine N-oxide. Hydrogcnolysis of the N-O bond followed by peracetylation led to the expected aminolyxose derivatives 14 and 16. A similar sequence, using 4 and the hydroxamic-acid derivative 18 of (+)-D-mandelic acid led, with a poor asymmetric induction, to a mixturc of the expected optically active aminolyxose compounds 19A/19B.

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“…After evaporation of the solvents, the oily residue was recrystalliLed (AcOEt/EtOH 95 :5): a colourless compound (4.5 g, 58%), m.p. 111-112" ( [40]: 107-109").…”

Section: Experimental Partmentioning

confidence: 99%

Syntheses of Diamino‐dideoxylyxose Derivatives using Acylnitroso Dienophiles

Defoin

Fritz

Schmidlin

et al. 1987

Helvetica Chimica Acta

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Ungewöhnliche Inhaltsstoffe des BlätterpilzesLyophyllum connatum (Agaricales)

Fugmann¹,

Steglich²

1984

Angew. Chem.

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Unusual Components of the Toadstool Lyophyllum connatum (Agaricales)

Fugmann

Steglich

1984

Angew. Chem. Int. Ed. Engl.

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thylformamide (DMF) afforded the desired glycopentapeptide allyl ester 9, whose structure was likewise confirmed by elemental analysis and spectroscopic data (I3C-NMR: 6= 102.9, C-1, Jp)c-H)= 163 Hz (dimethyl sulfoxide)).The allyl group has thus proven to be a valuable achiral carboxy-protecting group even for difficult peptide and glycopeptide syntheses, and can be used in conjunction with N-terminal Z -and Boc-protecting groups. Also noteworthy is that the four glycopeptide allyl esters 3a, 38, 6 and 9 are crystalline.

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Darstellung und Acylierungen von 1.1‐Dialkyl‐3‐hydroxyharnstoffen

Cited by 10 publications

References 11 publications

Syntheses of Diamino‐dideoxylyxose Derivatives using Acylnitroso Dienophiles

Syntheses of Diamino‐dideoxylyxose Derivatives using Acylnitroso Dienophiles

Ungewöhnliche Inhaltsstoffe des BlätterpilzesLyophyllum connatum (Agaricales)

Unusual Components of the Toadstool Lyophyllum connatum (Agaricales)

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