Synthesis and antimicrobial activities of two novel amino sugars derived from chloraloses

Newly synthesized furanoside-based NHC ligands for the arylation of aldehydes

“…36 In the present study, a new aminochloralose derivative (c) from D-mannose was synthesized by selective tosylation of the appropriate chloralose followed by azidation and reduction reactions ( Figure 1). 36,37 In the 1 H and 13 C NMR spectra of the compound c, the H-1 and HC-CCl 3 proton resonances were detected at 6.06 and 5.72 ppm and 106.1 and 110.1 ppm, respectively, while the OCH 3 protons were examined at 3.90 ppm. The imidazolium salts (2a-c) were prepared by a two-step procedure, using aminochloralose derivatives as starting reagents ( Figure 2).…”

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

“…The first members of this class are -andchloralose (or -glucochloralose) prepared via the reaction of anhydrous glucose and anhydrous chloral in the presence of sulfuric acid catalyst by Heffter [1] and the first time applied to therapeutics by Hanriot [2,3]. In addition to glucochloraloses, preparations of other chloraloses (xylochloralose [3,4], arabinochloralose [3,[5][6][7], galactochloralose [3,8] and mannochloralose [3,9]) have been also reported using the same synthetic method. All of chloraloses [3][4][5][6][7][8][9] synthesized so far contain 1,2-O-trichloroethylidene group in furanose form.…”

“…In addition to glucochloraloses, preparations of other chloraloses (xylochloralose [3,4], arabinochloralose [3,[5][6][7], galactochloralose [3,8] and mannochloralose [3,9]) have been also reported using the same synthetic method. All of chloraloses [3][4][5][6][7][8][9] synthesized so far contain 1,2-O-trichloroethylidene group in furanose form. Unlike most acetals, 1,2-O-trichloroethylidene acetals are very stable protecting group under acidic media because of inductive effects of trichloromethyl group and also stable in mild basic conditions.…”

“…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.…”

Synthesis, characterization, and biological evaluation of new N-glycosides derived from O-pivaloylated β-d-glucopyranosylamine

“…These derivatives, bearing nitrogen scaffolds in different ring positions on the sugar skeleton, are called N-glycosides, and many N-glycosides derivatives are of increasing interest because of their diverse biological properties such as antimicrobial [9], anti-inflammatory [10], anti-influenza [11], antiviral [12], and antitumor activities [13]. All this explains that certain series of N-glycosides are regarded as major target molecules for many years, owing to their biological and medicinal importance [14,15]. Therefore, studies of the synthesis and pharmacology of Nglycosides derivatives have attracted more interest in recent years [3,16,17].…”