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. 2020 Sep 18;76(Pt 10):1653-1656.
doi: 10.1107/S2056989020012438. eCollection 2020 Oct 1.

Crystal structure of 6-azido-6-de-oxy-1,2- O-iso-propyl-idene-α-d-gluco-furan-ose

Adam Wood  1   2 , Paul V Bernhardt  3 , Ian van Altena  1 , Michela I Simone  1   2
Affiliations

Crystal structure of 6-azido-6-de-oxy-1,2- O-iso-propyl-idene-α-d-gluco-furan-ose

Adam Wood et al. Acta Crystallogr E Crystallogr Commun. .

Abstract

Short syntheses to high Fsp 3 index natural-product analogues such as imino-sugars are of paramount importance in the investigation of their biological activities and reducing the use of protecting groups is an advantageous synthetic strategy. An iso-propyl-idene group was employed towards the synthesis of seven-membered ring imino-sugars and the title compound, C9H15N3O5, was crystallized as an inter-mediate, in which the THF ring is twisted and the dioxolane ring adopts an envelope conformation: the dihedral angle between the rings is 67.50 (13)°. In the crystal, the hydroxyl groups participate in O-H⋯(O,O) and O-H⋯N hydrogen-bonding inter-actions, which generate chains of mol-ecules propagating parallel to the a-axis direction. There is a notable non-classical C-H⋯O hydrogen bond, which cross-links the [100] chains into (001) sheets.

Keywords: azide; crystal structure; d-glucose; glycosidase inhibition; imino­sugar; regioselectivity; tosyl­ation.

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Figures

Figure 1
Figure 1
The mol­ecular structure of 3 showing 50% displacement ellipsoids.
Figure 2
Figure 2
Partial packing diagram for 3 showing hydrogen bonds as dashed lines.
Figure 3
Figure 3
Structure of 4 (see text).
See this image and copyright information in PMC

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