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: O-Tributylstannyl-D-glucal undergoes allylic oxidation when treated with N-iodosucinimide (NIS) in benzene, whereas oxidative 1,6-halocyclization occurs with NIS in acetonitrile or molecular halogens in various solvents.
Abstract: O-Tributylstannyl-D-glucal undergoes allylic oxidation when treated with N-iodosucinimide (NIS) in benzene, whereas oxidative 1,6-halocyclization occurs with NIS in acetonitrile or molecular halogens in various solvents.
TL;DR: In this article, polymer-supported electrophilic reagents are prepared which efficiently add to carbohydrate-derived glycals under very mild conditions, and 2-deoxy-2-halo-pyranosyl acetates or azides are generated in excellent yield.
Abstract: Polymer-supported electrophilic reagents are prepared which efficiently add to carbohydrate-derived glycals under very mild conditions. Depending on the hypervalent reagent initially employed for oxidizing polymer-bound halides 1a or 1b both acetoxyhalogenations or azidoiodination can be carried out. With sugar-derived glycals, 2-deoxy-2-halo-pyranosyl acetates or azides are generated in excellent yield. Free hydroxy groups are tolerated. Even, fully unprotected glucal 23 can be employed for the short synthesis of 2-deoxy-2-iodo glycosyl acetates 24a,b .
Patent•
15 May 2018
TL;DR: In this article, a synthetic method of acetylated delta-hydroxy-alpha, β-unsaturated furfural is disclosed, in which a glucal having a protective group, an organic solvent and water are mixed according to mole-volume ratio of 1 mol:50-250 L:0.6-2.8 L, a ring-opening reaction is performed by adopting FeCl3 as a catalyst, a product is mixed with triethylamine, DMAP and acetic anhydride according to a molar ratio of1:1-3:0
Abstract: A synthetic method of acetylated delta-hydroxy-alpha,beta-unsaturated furfural is disclosed. The method is characterized in that a glucal having a protective group, an organic solvent and water are mixed according to mole-volume ratio of 1 mol:50-250 L:0.6-2.8 L, a ring-opening reaction is performed by adopting FeCl3 as a catalyst, a product is mixed with triethylamine, DMAP and acetic anhydride according to a molar ratio of 1:1-3:0.1-0.5:0.5-3.0, the mixture is subjected to acetaylation at 0-45 DEG C, and neutralization, extraction and purification are performed after the reaction is finishedto obtain acetylated delta-hydroxy-alpha,beta-unsaturated furfural having different protective groups. Compared with the prior art, the method has characteristics of a simple process, convenient operation, nontoxic and economical agents, mild reaction conditions and a high reaction speed and a high yield, and is a green, economical and efficient novel acetylated Perlin aldehyde synthetic method having a good application prospect.
TL;DR: In this paper, the treatment of 3,4,6-tri-O -acetyl-d -glucal and unprotected d -GLucal with trimethylsilyl cyanide, under thermal conditions in the absence of catalyst, afforded the corresponding 2,3-unsaturated glycosyl cyanides in high yield.
Abstract: The treatment of 3,4,6-tri- O -acetyl- d -glucal and unprotected d -glucal with trimethylsilyl cyanide, under thermal conditions in the absence of catalyst, afforded the corresponding 2,3-unsaturated glycosyl cyanides in high yield.