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: A magnetic core-shell solid-acid catalyst Fe3O4@C-SO3H was used for synthesis of O-2,3-unsaturated glycosides through Ferrier rearrangement as mentioned in this paper.
Abstract: A magnetic core-shell solid-acid catalyst Fe3O4@C-SO3H was studied for synthesis of O-2,3-unsaturated glycosides through Ferrier rearrangement. The donors include 3,4,6-tri-O-acetyl- d -glucal and 3,4-di-O-acetyl- l -rhamnal. The acceptors consist of primary alcohols, secondary alcohols, tert-butanol, unsaturated alcohols, halogenated alcohol, sterol, sugars, and phenols. O-2,3-Unsaturated glycosides were obtained rapidly ( 5:1 to 19:1). Moreover, the catalyst can be easily separated from the reaction with an external magnetic force and reused for a minimum of five times without any significant decrease in the yields of the products after every recycle, suggesting it a promising green catalyst in 2,3-unsaturated glycosides syntheses.
9 citations
Patent•
22 Jan 1991
TL;DR: In this paper, a method of synthesizing novel glycosides, especially steroidal glycoside, and a novel method of their production, is provided, in which an alcohol or phenol, especially a hydroxy-steroid such as a water-insoluble cholesterol, is glycosylated, such that the glycosysylation is performed in a single step.
Abstract: Novel glycosides, especially steroidal glycosides, and a novel method of their production, are provided. For the novel method of producing novel glycosides, hydroxysteryl compounds are glycosylated with tri-O-acyl glucal using molecular iodine as a reaction catalyst. In this method an alcohol or phenol, especially a hydroxy-steroid such as a water-insoluble cholesterol, is glycosylated, such that the glycosylation is performed in a single step. The resulting steryl pyranoside is by oxidation converted to the corresponding 7-ketosteryl di-O-acyl-pyranoside. The latter pyranoside is selectively reduced to provide the corresponding 7-β-hydroxysteryl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside. The steroidal glycosides obtained in this way possess valuable pharmacological properties. In particular, the glycosides in vivo exhibit a selective cell-destructive activity on malignant cells which activity is substantially free of side effects on normal cells. The glycosides also possess a drive-enhancing (stimulating) activity and an anti-inflammatory (immunosuppressive or immunoregulatory) activity.
8 citations
TL;DR: The addition of the pseudohalogens nitryl iodide (NO2I), iodine nitrate (IONO2), and iodine azide (IN3) to the terminal, unsaturated sugar, methyl 5,6-dideoxy-2,3-di-O-ptolylsulfonyl-α-l -arabino-hex-5-enofuranoside (1,3,4,6) was described in this article.
8 citations
TL;DR: In this paper, the electrochemical bromination of 3,4,6-tri-O-acetyl-d -glucal has been investigated in DMSO by cyclic voltammetry and preparative-scale electrolyses.
8 citations
TL;DR: In this paper, a series of 2,3-unsaturated glycosides were obtained from 3,4,6-tri-O-acetyl-d -glucal or 3, 4,4-di-O -acetyl -l -rhamnal under mild reaction conditions in good yield and high anomeric selectivity.
8 citations