The Knoevenagel-Doebner Reaction on 1,2-O-(2,2,2-Trichloroethylidene) Derivatives of D-Gluco- and D-Manno- furanose

Abstract

The synthesis of new α,β-unsaturated furanuronic acid derivatives of α-gluco- (3), β-gluco- (6) and β-manno-chloraloses (9) via a convenient one pot procedure using the Knoevenagel-Doebner reaction approach are described. The dialdofuranose derivatives were reacted with malonic acid under Knoevenagel-Doebner reaction conditions and (E)-α,β-unsaturated furanuronic acid derivatives were obtained.

Synthesis and characterization of sugar-based methacrylates and their random copolymers by ATRP

“…Dimethylformamide (DMF, ≥99.8%, Sigma-Aldrich Chemical Corporation, Steinheim, Germany) was dried on 4A molecular sieve. Protected furanosidic sugars D-glufrn, D-manfrn, SD-glufrn, D-galfrn were prepared according to literature respectively [37][38][39][40]. TLC (thin layer chromatography) and column chromatography were performed on precoated aluminum plates (Merck 5554) and silicagel G-60 (Merck 9385) respectively.…”

Synthesis, characterization, and antimicrobial activities of novel monosaccharide-containing Schiff base ligands

“…Alternatively, the 1,2-O -trichloroethylidene acetal can be removed using a Raney nickel procedure. 11 They have proved to be suitable protecting groups for the synthesis of some biologically important compounds such as amines, 16 lactones, 17 orthoesters, 13,14 spiroendoperoxides, 18 spirodifuranose, 19 O -glycosides, 20 uranic acid, 21 oxime, 22 oxetanes, 23 Wittig products, 24 and Schiff base ligands. 25 As part of ongoing studies into the chemistry of monosaccharide trichloroethylidene acetals, we recently synthesized some ONO-tridentate chiral Schiff bases.…”

The Newest Member of the Family of Chloralose: Synthesis of β‐Ribochloralose and Some Derivatives

“…Chloraloses are also used as starting material for the synthesis of new compounds in carbohydrate chemistry due to potentially biological activity and stable protection in the 1,2-O-positions of theirs. Many derivatives of chloraloses have been reported such as amine [6], lactone [16], orthoesters [5,7,9], O-glycosides [7], dialdofuranose [9,17], uronic acids [17], Wittig products [18], oxime [19], spiroendoperoxide [20], thiosemicarbazone [21], and oxetane [22]. The most important ones of these derivatives, carbohydrate orthoesters, have been used very often as intermediate products in the synthesis of O-glycoside.…”