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Synthesis of C2-symmetrical polyhydroxyazepanes as inhibitors of glycosidases

✍ Scribed by Xinhua Qian; Francisco Morís-Varas; Chi-Huey Wong

Book ID
103983410
Publisher
Elsevier Science
Year
1996
Tongue
English
Weight
242 KB
Volume
6
Category
Article
ISSN
0960-894X

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✦ Synopsis

Two C2-symmetrical bis-epoxides were prepared from/2-mannitol and were subjected to nucleophilic displacements with allylamine and benzylamine. Initial intermolecular epoxide opening, followed by a preferred intramolecular 7-endo-tetragol cyclization, afforded protected polyhydroxyazepanes as major products. Compound 15 was found to inhibit seven different glycosidases with K i in the micromolar range.

📜 SIMILAR VOLUMES

Synthesis of C2-symmetric bis(cyclic iso
Synthesis of C2-symmetric bis(cyclic isothioureas) as potent inhibitors of glycosidases
✍ Laurence Gauzy; Yves Le Merrer; Jean-Claude Depezay; Dominique Damour-Barbalat; 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 210 KB

Enantiopure C2-symmetric bis(cyclic isothioureas), considered as potent inhibitors of glycosidases, have been synthesized from D-mannitol. The key step involved a mercuriccatalyzed transformation of a cyclic 1,3-thiazolidine-2-thione into a 2-N-tert-butylamino-1,3thiazoline.