Topic
Glucal
About: Glucal is a research topic. Over the lifetime, 590 publications have been published within this topic receiving 8960 citations. The topic is also known as: D-glucal.
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TL;DR: With hydrazine 1,6-anhydro-2-azido-2deoxy-D-glucopyranose (1,6)-Derivate as discussed by the authors, having an axial azido group, in an inhomogeneous reaction yields the 2-deoxy compound (2) and the glucal (3).
Abstract: 1,6-Anhydro-2-azido-2-desoxy-D-glucopyranose-Derivate (1) mit axialer Azidogruppe reagieren mit Hydrazin uneinheitlich zu 2-Desoxy-Verbindungen (2) und Glucalen (3). Das Glucosid 7 mit aquatorialer Azidogruppe ergibt mit Hydrazin die Desoxy-Verbindung 9. Zur Gewinnung von 1,5-Anhydropentiten 18,19 aus Pentopyranosylaziden 15, 16 ist die Reaktion mit Hydrazin geeignet.
Hydrazine Reactions, XIV. Reactions of Azido Sugars with Hydrazine
With hydrazine 1,6-anhydro-2-azido-2-deoxy-D-glucopyranose (1), having an axial azido group, in an inhomogeneous reaction yields the 2-deoxy compound (2) and the glucal (3). Under similar conditions with glucoside 7, having an equatorial azido group, the deoxy compound 9 is obtained. The same reaction is suitable for the preparation of 1,5-anhydropentitols 18 and 19 from pentopyranosyl azides 15 and 16.
9 citations
TL;DR: In this paper, the synthesis of (5 R, 7 S, 13 S )- and (5 S, 7 S, 13S )-13-methoxy-1,6,8-trioxadispiro[4.1.5] pentadecane from tri- O -acetyl- d -glucal, by a convenient homologation of C-1 and C-6 atoms which led to an appropriate dihydroxyl intermediate 7, is reported.
Abstract: The synthesis of (5 R , 7 S , 13 S )- and (5 S , 7 S , 13 S )-13-methoxy-1,6,8-trioxadispiro[4.1.5.3] pentadecane from tri- O -acetyl- d -glucal, by a convenient homologation of C-1 and C-6 atoms which led to an appropriate dihydroxyl intermediate 7 , is reported. The key steps for the construction of the two spiroacetal systems involved a double, step by step, radical abstraction promoted by (diacetoxyiodo)benzene and iodine.
9 citations
TL;DR: The catalyst CeCl3·7H2O-NaI and ligand L-proline in toluene, was found to be much more efficient and high atom economic for the stereoselective glycosidation of prop argyl alcohol with glucal, afforded exclusively α-2-deoxy propargyl glycoside in 98% optimized yield.
9 citations
01 Nov 2016
TL;DR: Stannyl derivatives of 2-alkenyl acetylated D-glucals have been synthesized via palladium-catalyzed regioselective hydrostannation in good yields under mild reaction conditions.
Abstract: Stannyl derivatives of 2-alkenyl acetylated D-glucals have been synthesized via palladium-catalyzed regioselective hydrostannation in good yields under mild reaction conditions. Factors affecting the regioselectivity of hydrostannation including chelation by the neighbouring acetyl-oxygen and the electronic effect of the substituent R on alkyne have been evaluated. The synthetic applications of these stannyl derivatives of D-glucal are shown by performing Stille and Sonogashira cross-coupling reactions to obtain a library of substituted 2-alkenyl derivatives of D-glucal.
9 citations
TL;DR: In this paper, the first report on aza-Ferrier rearrangement using molecular iodine is presented, which makes this method simple, convenient, and cost-effective, and the use of iodine makes the method simple and convenient.
9 citations