Stable spiro-endoperoxides by sunlight-mediated photooxygenation of 1,2-O-alkylidene-5(E)-eno-5,6,8-trideoxy-α-d-xylo-oct-1,4-furano-7-uloses

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

“…A two pot alternative synthesis of similar compounds has been reported previously [ 27 , 31 , 33 ]. Hence, now we report synthesis of α,β -unsaturated furanuronic acid derivatives via a more facile one pot procedure using the Knoevenagel-Doebner reaction approach.…”

“…Compound 4 was purchased from Sigma-Aldrich Corp. and purified via crystallization from boiling methanol. Syntheses of ( R )-1,2- O- (2,2,2-trichloroethylidene)- α -D- xylo -1,4-furanodialdose ( 2 ) from 1 , ( S )-1,2- O- (2,2,2-trichloroethylidene)- α -D- xylo -1,4-furanodialdose ( 5 ) from compound 4 were performed according to the literature via periodate oxidation reaction [ 31 , 33 ]. Compound 7 was synthesized from D-mannose and chloral according to the literature procedure [ 19 ].…”

“…In addition to the well-known effects of chloraloses, arabinochloralose has been used as an intermediate compound for the development of new antituberculosis drugs in pharmaceutical research [ 29 ]. Spiro -endoperoxide chloraloses [ 30 , 31 ] and aminochloraloses [ 32 ] were synthesized and investigated antimicrobial activity against some microorganisms.…”

Synthesis, Characterization, and Thermokinetic Analysis of New Epoxy Sugar Derivative

“…It is not possible to make an epoxy derivative of -chloralose without using the protecting group (5,6-O-isopropylidene). 1,2-O-(R)-Trichloroethylidene--D-glucofuranose was further acetalized with 2,2-dimethoxypropane (2,2-DMP) to give the 5,6-O-isopropylidene derivative (compound 1) [9]. This sugar derivative has only one free hydroxyl group which can be etherified.…”

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.…”