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: In this paper, the reaction of chlorine with a suspension of D-glucal triacetate and silver monofluoride in an acetonitrile/benzene solution, affords a mixture of the four possible 2-chloro-2-deoxy-D-glycopyranosyl fluoride triacetates.
Abstract: Reaction of chlorine with a suspension of D-glucal triacetate and silver monofluoride in an acetonitrile/benzene solution, affords a mixture of the four possible 2-chloro-2-deoxy-D-glycopyranosyl fluoride triacetates. The structures of these derivatives have been established by nuclear magnetic resonance studies and confirmed by independent syntheses. The major product is 2-chloro-2-deoxy-β-D-glucopyranosyl fluoride triacetate. These results are compared with those from the related "BrF" and "IF" additions.
7 citations
TL;DR: An efficient and concise method for the construction of various O-glycosidic bonds by a palladium-catalyzed reaction with a 3-O-picoloyl glucal was developed in this paper.
Abstract: An efficient and concise method for the construction of various O-glycosidic bonds by a palladium-catalyzed reaction with a 3-O-picoloyl glucal is developed.
7 citations
TL;DR: In this paper, a method for the preparation of 2-deoxy-d-glucose and purin-9-yl 2-Deoxy-α-d -glucopyranonucleosides was developed.
Abstract: Convenient and stereoselective methods for the preparation of 2-deoxy- d -glucose and purine 2-deoxy-α- d -glucopyranonucleosides were developed. Halogen-mediated O-glycosidation of d -glucal by bromine in MeOH followed by reductive removal of the halo group and hydrolysis of methoxy group by zinc in saturated aqueous sodium dihydrogen phosphate gave 2-deoxy- d -glucose. Treatment of 3,4,6-tri-O-acetyl- d -glucal with IBr and 2,6-dichloropurine based on haloetherification and subsequent reductive removal of iodine and deprotection allowed the isolation of purin-9-yl 2-deoxy-α- d -glucopyranonucleoside. Preparation of several purin-9-yl 2-deoxy-α- d -glucopyranoside derivatives is also reported. Their configuration was confirmed by single crystal X-ray analysis of the key intermediate 2,6-dichloro-9-(2-iodo-2-deoxy-α- d -glucopyranosyl)purine.
7 citations
TL;DR: The results indicate that a second function of AMP is the formation of the phosphate binding pocket in the enzyme-glucal-glycogen-AMP complex.
7 citations
TL;DR: The same procedure proved to be appropriate in synthesizing dihydropyran derivatives ('C-glycosides') using allyltrimethylsilane as the nucleophile (only 'α-anomers' were obtained). All new compounds were fully characterized by spectral data, whereas single-crystal X-ray analysis was performed for two thioglycosides.
7 citations