Starting with methyl 4,6‐O‐benzylidene‐α‐D‐glucopyranoside (4), an optimized procedure is reported for preparation of the bromide 7, which is transformed into the N‐acylated heptopyranosamine 9. After introduction of an axially positioned azido moiety in position 3 intramolecular N/O‐acetal formation succeeds to provide the morphan analogue 17. In receptor binding studies with radioligands the amines 18b‐18d reveal higher affinity for μ‐receptors than for κ‐receptors. The most μ‐active compound 18b (Ki = 14 nM) contains two aryl substituents, which presumably may occupy both aryl binding sites of μ‐receptors.

中文翻译：

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新型氨基取代吗啡类似物的合成和阿片受体结合

从甲基 4,6 - O - 亚苄基 - α - D - 吡喃葡萄糖苷 (4) 开始，报道了制备溴化物 7 的优化程序，将其转化为 N-酰化吡喃庚糖胺 9。引入轴向定位的叠氮基后3 位分子内 N/O-缩醛形成的部分成功提供吗啡类似物 17。在用放射性配体的受体结合研究中，胺 18b-18d 显示对 μ-受体的亲和力高于对 κ-受体的亲和力。μ-活性最强的化合物 18b (Ki = 14 nM) 含有两个芳基取代基，可能占据 μ-受体的两个芳基结合位点。