178964-38-0

Upstream product

• 71223-75-1 3,4-di-O-allyl-1,2:5,6-dianhydro-D-mannitol 
• 100-46-9 benzylamine 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 71240-67-0 3,4-di-O-allyl-D-mannitol 
• 58315-80-3 3,4-di-O-allyl-1,2:5,6-di-O-isopropylidene-D-mannitol 

Relevant academic research and scientific papers

C2-symmetrical tetrahydroxyazepanes as inhibitors of glycosidases and HIV/FIV proteases.

C2-Symmetrical tetrahydroxyazepanes were synthesized as inhibitors for glycosidases. Tetrahydroxyazepane 1 is a non-specific inhibitor of various glycosidases, while compounds 2, 3 and 4 specifically inhibit beta-N-acetylglucosaminidase, beta-glucosidase, and alpha-fucosidase, respectively, with Ki in the micromolar range. Compound 1 is not an inhibitor of HIV/FIV proteases, but its 3,6-difluorobenzyl derivatives are moderate inhibitors of both enzymes.

Synthesis of C2-symmetrical polyhydroxyazepanes as inhibitors of glycosidases

Two C2-symmetrical bis-epoxides were prepared from D-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.