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: The unique reactive intermediate formed in the 3,4,6,tri-O•O•benzyl•d−glucal−TfOH (triflic acid)-n•Bu4NI reaction system (in dichloromethane) reacted with nucleophiles in a regio-and stereoselective manner as mentioned in this paper.
Abstract: The unique reactive intermediate formed in the 3,4,6‐tri‐O‐benzyl‐d‐glucal–TfOH (triflic acid)–n‐Bu4NI reaction system (in dichloromethane) reacted with nucleophiles in a regio‐ and stereoselective manner. These selectivities resulted in hitherto unknown compounds, such as benzyl 4,6‐di‐O‐benzyl‐2,3‐dideoxy‐3‐iodo‐α‐glucopyranoside, which was obtained in the presence of an iodide ion as a nucleophile. The corresponding 2‐deoxy α‐glycosides were obtained exclusively in the corresponding reaction with hydroxylic nucleophiles.
TL;DR: A very efficient Pd(OAc)2 catalyzed copper and ligand free Sonogashira coupling reaction is developed and its application in high-performance liquid chromatography is described.
Abstract: A very efficient Pd(OAc)2 catalyzed copper and ligand free Sonogashira coupling reaction is developed.
TL;DR: In this article, an unprotected enones derived from d -glucal reacted with trimethylsilyl cyanide in the presence of a catalytic amount of a palladium compound in 1,4-addition fashion to afford the corresponding 3-keto-glycosyl cyanides in high yield and in high α-selectivity.
Abstract: Acetylated and unprotected enones derived from d -glucal reacted with trimethylsilyl cyanide in the presence of a catalytic amount of a palladium compound in 1,4-addition fashion to afford the corresponding 3-keto-glycosyl cyanides in high yield and in high α-selectivity.
TL;DR: Iodophosphoryloxylation of carbon-carbon multibonds was attempted in this article, and 2-deoxy-2-iodoglycosyl diphenylphosphinates were obtained from the corresponding glycals.
Abstract: Iodophosphoryloxylation of carbon-carbon multibonds was attempted. Alkynes and cyclohexene were converted to the corresponding 1,2-iodophosphoryloxylated compounds in moderate to good yields with a trivalent iodine compound/iodine system, while glucal gave mainly the corresponding iodohydrin compound in this system. However, 2-deoxy-2-iodoglycosyl diphenylphosphinates were obtained from the corresponding glycals with a diphenylphosphinic acid/iodine/potassium carbonate system in good yields. Moreover, triethylborane smoothly reduced 2-deoxy-2-iodoglycosyl diphenylphosphinates to 2-deoxyglycosyl diphenylphosphinates in a 1,4-cyclohexadiene solvent.