On the way to liposidomycins, new nucleoside antibiotics. Access to the homochiral diazepanone core

Journal of Carbohydrate Chemistry

Volumn 16, Issue 2, 1997, Pages 129-141

  Gravier Pelletier, Christine ^a   Charvet, Isabelle ^a   Le Mener, Yves ^a   Depezay, Jean Claude ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031483465     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328309708006515     Document Type: Article

References (25)

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19. In a preliminary study, we observed that during the opening of 7b by the methyl N-methyl-L-phenylalaninate, intramolecular transesterification reactions occurred. Such reactions were avoided by N-benzyl protecting the secondary amine on one hand and by using the tert-butyl N-methyl phenylalaninate on the other hand.
20. 13C NMR (63 MHz) spectra.
21. 8 could also be obtained in 62% yield in presence of ytterbium triflate at 20 °C in two weeks; see 10b.
22. This transformation can also be performed by hydrogen in presence of Pd/C 10%, but required longer reaction time which led to partial epimerization.
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24. 2) instead of a secondary one (RNHMe) should occur in a better yield (71%) according to reference 6.
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