Synthesis of trehazolin .BETA.-anomer.

Synthesis and Biological Activity of Natural Aminocyclopentitol Glycosidase Inhibitors: Mannostatins, Trehazolin, Allosamidins, and Their Analogues

“…The key intermediate 64 was subjected to nucleophilic opening with sodium mercaptide which proceeded smoothly to give two regiomeric thioethers 65a and 65b which were obtained in equal amounts but easily separated. Removal of the protecting groups of the latter thioethers gave the target 3-epimannostatin (66) and its positional isomer 67, respectively, as their hydrochloride salts. The analogues were synthesized in 18 steps with overall yields of 1.68% and 1.5%, respectively.…”

“…Shiozaki's group has reported the preparation of the trehazolin β-anomer 155 (the C-1′ epimer) 66 and of the aminopropanediol derivative 156 67 Knapp and collaborators 61 have reported the (1f4)linked pseudodisaccharide 164, the first in a series of novel analogues coined "trehazoloids" (Scheme 24).…”

A Highly Efficient Pinacol Coupling Approach to Trehazolamine Starting from d-Glucose

“…Trehazolin probably acts as a close mimic of the substrate α,α-trehalose ( 1 ) or, more likely, of the postulated glycopyranosyl cation intermediate involved in the hydrolytic step of glycosides or a transition state leading to it. By systematic chemical modifications of the sugar 10 and the aglycon, 6b,d,10d, a number of structure−activity relationships have been established. All previous total syntheses of 2 6b,d,7a,c,9 followed a general retrosynthetic strategy where the molecule is assembled by linking a protected α- d -glucosyl isothiocyanate ( 4 ) 9,12 to free or partially protected aminocyclopentitol 3 .…”