Tricyclic furanoid dichloroacetyl orthoesters of d-mannose from 1,2-O-trichloroethylidene-β-d-mannofuranose

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.…”

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.…”

“…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. But, it is unstable against strong bases such as potassium tert-butoxide and is converted to most reactive ketene acetals [5,9]. The only method for the removal of this protecting group has been reported as Raneynickel procedure [10].…”

“…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.…”