Syntheses of tetrahydroxyazepanes from chiro-inositols and their evaluation as glycosidase inhibitors

Vorschau auf Heft 3/2016

“…The same procedure as 1a using 2,3,4,5‐tetra‐ O ‐benzyl‐ L ‐iditol36 (331 mg, 0.611 mmol) in place of 2,3,4,5‐tetra‐ O ‐benzyl‐ D ‐mannitol gave a 71:29 mixture of the title compound, and DMSO as yellow oil; yield: 349 mg (quant.). 1 H and 13 C NMR were identical to those reported 37. This oil was used for the next reaction, without further purification.…”

Crystal structure of (4R,5S,6R)-6-azido-5-benzyloxy-3,3,4-trifluoroazepan-1-ium 2,2,2-trifluoroacetate from synchrotron data

“…Substituted azepane rings are prevalent in many bioactive natural compounds (Wipf & Spencer, 2005;Nú ñ ez-Villanueva et al, 2011). Recently, substituted azepane rings and related compounds (iminocyclitols or iminosugars) have attracted considerable attention from medicinal chemists because of their great potential as glycosidase inhibitors (Stü tz, 1999) and antidiabetic (Painter et al, 2004), anticancer (Zitzmann et al, 1999) and antiviral agents (Laver et al, 1999) and are also effective against HIV (Sinnott, 1990). The conformational control of such flexible ring structures is important to their bioactivity.…”

N‐Heterocyclic Carbene‐Catalyzed Benzoin Strategy for Divergent Synthesis of Cyclitol Derivatives from Alditols

“…1 H and 13 C NMR were identical to those reported. [38] This oil was used for the next reaction, without further purification.…”

“…To a suspension of triazolium salt ent-10 (14 mg, 0.030 mmol) in toluene (6 mL), a 10% v/v solution of Et 3 N in toluene (0.04 mL, 0.03 mmol) was added at rt. After 30 min, 1b [38] (160 mg, 0.290 mmol) in toluene (3 mL + 1.5 mL wash % 2) was added. After 18 h, the mixture was concentrated in vacuo.…”