Synthesis of 6-amino-6-deoxy- d-gulono-1,6-lactam and l-gulono-1,6-lactam derived from corresponding 5,6- O-sulfinyl hexono-1,4-lactones

Syntheses of 6-amino-6-deoxy-2,3- O-isopropylidene- d-gulono- and l-gulono-1,6-lactams 3 and 4 from corresponding glycono-1,4-lactones are described. Activation of the primary hydroxyl group requires 5,6-cyclic sulfite intermediate to obtain 6-azido-6-deoxy derivatives, which are cyclized after redu...

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Bibliographic Details
Published in:Tetrahedron 2006-07, Vol.62 (31), p.7455-7458
Main Authors: Gireaud, Laurent, Chaveriat, Ludovic, Stasik, Imane, Wadouachi, Anne, Beaupère, Daniel
Format: Article
Language:English
Subjects:
5,6- O-Sulfinyl-1,4-lactone
6-Amino-6-deoxy- d-gulonolactam
6-Amino-6-deoxy- l-gulonolactam
d-Gulono-1,4-lactone
l-Gulono-1,4-lactone
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Summary:Syntheses of 6-amino-6-deoxy-2,3- O-isopropylidene- d-gulono- and l-gulono-1,6-lactams 3 and 4 from corresponding glycono-1,4-lactones are described. Activation of the primary hydroxyl group requires 5,6-cyclic sulfite intermediate to obtain 6-azido-6-deoxy derivatives, which are cyclized after reduction. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2006.05.017