Synthesis of Aza-C-disaccharides (Dideoxyimino-alditols C-Linked to Monosaccharides) and Analogues

Abstract

The first aza-C-disaccharide (D-azaMan-b-CH 2 -(1→6)-D-Man-a-OMe) that mimicks a-D-Manp-(1→6)-a-D-ManOMe was made in 1994 by Johnson and coworkers. Several synthetic approaches to these disaccharide mimetics have been proposed. These are reviewed and compared. Several strategies rely on C-C bond forming reactions such as the Miyaura-Suzuki cross-coupling, the SmI 2 Barbier reaction, the addition of acetylides to aldonolactones, the cross-aldol reaction or the Michael addition of 7-oxabicyclo[2.2.1]heptanone derivatives ('naked sugars'), with subsequent formation of the iminoalditol moieties. Other approaches use nitrogen-containing systems such as sugar-derived nitrones or iminoaldoses that are coupled by either Wittig olefinations, cross-aldol reactions or Takai-Oshima-Nozaki-Kishi reactions. When available, the conformational analysis of the aza-C-disaccharides, as well as their inhibitory activities toward glycosidases, will be summarized.

Amine-linked diglycosides: Synthesis facilitated by the enhanced reactivity of allylic electrophiles, and glycosidase inhibition assays

“…These diglycosides showed weaker glycosidase inhibitory activity than the related N -substituted (monosaccharidic) altrosides recently reported by Jenkins et al [47]. These results are in accordance with those reported for other disaccharide mimetics, such as aza-C-disaccharides, which showed no significant inhibition towards commercially available glycosidases [48]. …”

Synthesis of 1,4-imino-L-lyxitols modified at C-5 and their evaluation as inhibitors of GH38 α-mannosidases

“…During the years, many scaffolds based on monosaccharides [4], disaccharides or higher oligosaccharides [5–6] as well as multivalent [7–8] carbohydrate units have been developed. These glycomimetics and glycopeptides have also found applications as bioactive compounds [9–10].…”

Synthesis , Characterization and computional study of Some New Aniline oxide derivatives

“…Treatment of the Synthesis of N-(4-(5-(furan-2-yl)-4,5-dihydro-1H-pyrazol-3yl)phenyl) hydroxylamine (1) with aldehydes(2)(3)(4)(5)(6) in the presence of p-toluene sulphonic acid as catalyst in boiling ethanol gave, after purification from(2)(3)(4)(5)(6) in 73-85% yield,as crystalline compounds (Scheme 5).The structures of these products were established from their elemental analysis, FT-IR, and 1 H NMR .The FT-IR spectra of N-(4-(5-(furan-2-yl)-4,5-dihydro-1H-pyrazol-3-yl)phenyl) hydroxylamine and aniline oxide compounds were characterized by the disappearance of the absorption band that was attributed to the (C=O) stretching which appeared at (1672-1710) cm -1 . These fact confirmed the correct expected chemical structure of these compounds.…”