Wood Adam, Bernhardt Paul V, van Altena Ian, Simone Michela I
Discipline of Chemistry, University of Newcastle, Callaghan, NSW 2308, Australia.
Priority Research Centre for Drug Development, University of Newcastle, Callaghan, NSW 2308, Australia.
Acta Crystallogr E Crystallogr Commun. 2020 Sep 18;76(Pt 10):1653-1656. doi: 10.1107/S2056989020012438. eCollection 2020 Oct 1.
Short syntheses to high 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, CHNO, 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 axis direction. There is a notable non-classical C-H⋯O hydrogen bond, which cross-links the [100] chains into (001) sheets.
短合成路线制备高指数天然产物类似物，如亚氨基糖，对于研究其生物活性至关重要，减少保护基团的使用是一种有利的合成策略。一个异亚丙基用于合成七元环亚氨基糖，标题化合物CHNO作为中间体结晶，其中四氢呋喃环扭曲，二氧戊环采取信封式构象：环之间的二面角为67.50 (13)°。在晶体中，羟基参与O-H⋯(O,O)和O-H⋯N氢键相互作用，形成平行于轴方向传播的分子链。存在一个显著的非经典C-H⋯O氢键，它将[100]链交联成(001)片层。
