Regioselective facile one-pot Friedländer synthesis of sugar-based heterocyclic biomolecules

Studies on the synthesis of ether-, substituted alkyl-, or aryl-linked C-disaccharide derivatives

“…Abbreviations such as, 'Sac', 'Ar' and 'Alk' correspond to 'Saccharide', 'Aromatic' and 'Alkenic' protons, respectively. Compounds 1a, 1c, 1d and 1e were synthesized by adopting procedures reported in the literature, [17][18][19][20][24][25][26] and the purity of these samples was found to be satisfactory. The synthetic procedure for 1b is as follows: To a solution of 4,6-O-benzylidene-D-glucopyranose (2.68 g, 10.0 mmol) in 1:9 H 2 O-THF were added NaHCO 3 (3.36 g, 4 equiv) and 2,4-pentadienone (2.0 g, 2 equiv).…”

“…[24][25][26] Although the synthesis of 1-C-b-D-glycosylic ketones are described in the literature, [24][25][26] in the present report we have extended the methodology to partially protected sugar derivatives such as 1-C-(4,6-O-butylidene-b-D-glucopyranosyl)propane-2-one (1a) [17][18][19][20] and 1-C-(4,6-O-benzylidene-b-D-glucopyranosyl)propane-2-one (1b).…”

“…[13][14][15][16] In order to study the weak interactions that exist in carbohydrates, it becomes increasingly important to understand the nature of the packing forces. In a continuation of our on-going research in the area of saccharide chemistry, [17][18][19][20] we report herein the facile synthesis of ether-, substituted alkyl-, or aryl-linked Cdisaccharide derivatives and the steric factors involved in the aldol condensation of these 1-C-b-D-glycosylic ketones with various ether linked dialdehydes. The existence of inter-and intramolecular hydrogen bonding interactions has also been studied using single-crystal XRD studies.…”

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

“…A sugar‐based ketone derivative has also been utilized in the Friedländer reaction of 2‐amino‐3‐formylchromone by Nagarajan et al., with which a 2‐(β‐ d ‐glucopyranosylmethyl)‐6,8‐dibromoquinoline derivative 97 could be obtained in 70 % yield with the aid of 25 mol % of pyrrolidine catalyst in a mixed solvent composed of dichloromethane and methanol (Scheme ).…”

Rational Design of Heterocyclic Moieties Incorporated in [1,2,3]Sugar‐Triazole Derivatives for Antioxidant Studies

“…[4] Drug development studies shows that glycosylated products play a vital role and also reliable platforms for the innovation of many of our existing front-line drugs. [5,6] Thus, the development of synthetic carbohydrate-based small molecules is increasingly being recognized as a viable and appealing approach towards the safe and effective therapeutics, [7,8] particularly glyco-hybrids containing heterocyclic moieties are great significance in the design and development of the new drugs. [9,10] Several carbohydrate derivatives have been reported in the literature [5] are known to possess good therapeutic profiles including solubility, in-vivo stability, target-binding affinity, and cell permeability.…”