### Synthesis and X-ray Structure of (2R,3R,4R,5R)-3,4,5-Tris-Benzyloxy-2-Benzyloxymethyl-Piperidin-1-ol, the N-Hydroxy-Analog of 2,3,4,6-Tetra-O-Benzyl-1-Deoxymannojirimycin.

The title compd. 8 was obtained for the first time by hydride-mediated redn. of the D-fructose-derived nitrone 9. The N-hydroxy piperidine 8 is a precursor of the N-hydroxy analog of DMJ, a potent inhibitor of $\alpha$-mannosidases. It was isolated as colorless crystals (triclinic, P1 space group) exhibiting the following cell parameters: a = 9.947(2) {\AA}; b = 12.155(2) {\AA}; c = 13.864(5) {\AA}; $\alpha$ = 100.98(3)°; $\beta$ = 97.94(2)°; $\gamma$ = 109.50(1)°. The X-ray anal. of a monocrystal of 8 allowed confirmation of its relative configurations and showed the anti orientation of its N-hydroxy group. This structural feature should be useful for considering the interaction of N-hydroxy imino-sugars with the recognition site of carbohydrate processing enzymes. Index Abstr. The title compd. 8 was prepd. for the first time by hydride-mediated redn. of the d-fructose-derived nitrone 9. Compd. 8 is a precursor of the N-hydroxy analog of DMJ, a potent inhibitor of $\alpha$-mannosidases. The X-ray anal. allowed confirmation of the relative configurations of 8 and showed the anti orientation of its N-hydroxy group. This structural feature will be useful for considering the interaction of N-hydroxy-imino-sugars with specific biol. targets. [on SciFinder(R)]

### Références

Titre
Synthesis and X-ray Structure of (2R,3R,4R,5R)-3,4,5-Tris-Benzyloxy-2-Benzyloxymethyl-Piperidin-1-ol, the N-Hydroxy-Analog of 2,3,4,6-Tetra-O-Benzyl-1-Deoxymannojirimycin.
Type de publication
Article de revue
Année de publication
2009
Revue
J. Chem. Crystallogr.
Volume
39
Pagination
494–499
ISSN
1074-1542
Soumis le 12 avril 2018