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

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.

SUBMITTER: Wood A

PROVIDER: S-EPMC7534240 | biostudies-literature | 2020 Oct

REPOSITORIES: biostudies-literature

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

Wood Adam A Bernhardt Paul V PV van Altena Ian I Simone Michela I MI

Acta crystallographica. Section E, Crystallographic communications 20200918 Pt 10

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 ...[more]

PMID: 33117583

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