Enantiospecific synthesis of the immunopotentiators erythro-9 (2-hydroxy-3-nonyl) hypoxanthines and the threo-diastereomers

Enantiospecific synthesis of the immunopotentiators erythro-9 (2-hydroxy-3-nonyl) hypoxanthines and the threo-diastereomers

The title compounds were prepared enantiospecifically by kinetic resolution of (+/-) l-nonene-3ol via Sharpless oxidation. The products 1,2R-epoxy-nonane-3S-ol and l-nonene-3R-ol were efficiently converted to all four stereoisomers of 2-hydroxy-3-nonylamine, which were subsequently incorporated into...

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Veröffentlicht in:Tetrahedron letters 1984, Vol.25 (51), p.5899-5902
Hauptverfasser: Bessodes, M., Abushanad, E., Antonakis, K.
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Preparations and properties
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Zusammenfassung:The title compounds were prepared enantiospecifically by kinetic resolution of (+/-) l-nonene-3ol via Sharpless oxidation. The products 1,2R-epoxy-nonane-3S-ol and l-nonene-3R-ol were efficiently converted to all four stereoisomers of 2-hydroxy-3-nonylamine, which were subsequently incorporated into the target hypoxanthines to evaluate their immunopotentiating activity.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(01)81715-9