کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1388564 | 1500904 | 2008 | 12 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: Synthetic studies towards a new scaffold, spirobicycloimidazoline Synthetic studies towards a new scaffold, spirobicycloimidazoline](/preview/png/1388564.png)
A new scaffold consisting of a carbocycle and a substituted imidazoline in an orthogonal arrangement was synthesized as a potential specific inhibitor of glycosidases. The spirobicycloimidazoline, (5R,6R,7R,8R)-8-(hydroxymethyl)-2-phenyl-1,3-diazaspiro[4.4]non-1-ene-6,7-diol, was synthesized from methyl 2-O-p-methoxybenzyl-3,4-di-O-benzyl-α/β-d-gluco-6-enopyranoside via (1R,2S,3S,4R,5S)-3,4-bis(benzyloxy)-2-(4-methoxybenzyloxy)-5-vinyl-cyclopentanol. The ring contraction of the 6-enopyranoside in the presence of zirconocene equivalent (‘Cp2Zr’) reagent gave exclusively the corresponding cyclopentanol without cleavage of the PMB protecting group. In the course of the study, a new α-mannosidase inhibitor, (1R,2R,3R,5R)-5-amino-3-hydroxymethyl-cyclopentane-1,2-diol, was also discovered.
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Journal: Carbohydrate Research - Volume 343, Issues 10–11, 21 July 2008, Pages 1624–1635