227458-60-8

Usage

Uses

Used in Medicinal Chemistry:
(2R,3S,4S,5R,6S)-3,4,6-TRIHYDROXY-2-HYDROXYMETHYL-7,9-DIAZA-1-OXA-SPIRO[4,5]DECANE-10-ONE-8-THIONE is used as a pharmaceutical candidate for the development of new drugs due to its unique structure and functional groups. The multiple hydroxy groups can form hydrogen bonds with biological targets, while the thione group can be involved in various chemical reactions to modify the compound's properties and activity.
Used in Material Science:
In the field of material science, (2R,3S,4S,5R,6S)-3,4,6-TRIHYDROXY-2-HYDROXYMETHYL-7,9-DIAZA-1-OXA-SPIRO[4,5]DECANE-10-ONE-8-THIONE can be used as a building block for the synthesis of new materials with specific properties. (2R,3S,4S,5R,6S)-3,4,6-TRIHYDROXY-2-HYDROXYMETHYL-7,9-DIAZA-1-OXA-SPIRO[4,5]DECANE-10-ONE-8-THIONE's complex structure and diverse functional groups can be exploited to create materials with unique characteristics, such as improved stability, reactivity, or selectivity.
Used in Chemical Research:
(2R,3S,4S,5R,6S)-3,4,6-TRIHYDROXY-2-HYDROXYMETHYL-7,9-DIAZA-1-OXA-SPIRO[4,5]DECANE-10-ONE-8-THIONE is used as a subject of chemical research to explore its reactivity, properties, and potential applications. (2R,3S,4S,5R,6S)-3,4,6-TRIHYDROXY-2-HYDROXYMETHYL-7,9-DIAZA-1-OXA-SPIRO[4,5]DECANE-10-ONE-8-THIONE's unique structure and functional groups make it an interesting target for further study, which can lead to the discovery of new reactions, mechanisms, and applications in various fields of science and industry.

Upstream product

• 227458-59-5 (2R,3R,4S,5R,6S)-3,4,5-triacetoxy-2-acetoxymethyl-7,9-diaza-1-oxa-spiro[4,5]decane-10-one-8-thione 
• 286369-08-2 (2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-2-benzoyloxymethyl-7,9-diaza-1-oxa-spiro[4,5]decane-10-one-8-thione 
• 82469-74-7 2,3,4,6-tetra-O-acetyl-1-deoxy-1-bromo-β-D-glycopyranosyl cyanide 
• 223261-77-6 C-(2,3,4,6-tetra-O-acetyl-1-bromo-1-deoxy-β-D-glucopyranosyl)formamide 
• 286369-05-9 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl cyanide 
• 286369-06-0 2,6-anhydro-3,4,5,7-tetra-O-benzoyl-D-glycero-D-gulo-heptonamide 
• 262849-68-3 C-(2,3,4,6-tetra-O-benzoyl-1-bromo-1-deoxy-β-D-glucopyranosyl)formamide 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 

Relevant academic research and scientific papers

Synthesis of and a comparative study on the inhibition of muscle and liver glycogen phosphorylases by epimeric pairs of D-gluco- and D-xylopyranosylidene-spiro-(thio)hydantoins and N-(D-glucopyranosyl) amides

D-Gluco- and D-xylopyranosylidene-spiro-hydantoins and -thiohydantoins were prepared from the parent sugars in a six-step, highly chemo-, regio-, and stereoselective procedure. In the key step of the syntheses C-(1-bromo-1-deoxy-β-D-glycopyranosyl)formami

Gram-scale synthesis of a glucopyranosylidene-spiro-thiohydantoin and its effect on hepatic glycogen metabolism studied in vitro and in vivo

A high yielding, simple synthesis is described starting from D-glucose to produce gram quantities of a glucopyranosylidene-spiro-thiohydantoin. This compound efficiently inhibited the activity of rat liver glycogen phosphorylase a; moreover, it also activated phosphorylase phosphatase which, in turn, decreased the amount of glycogen phosphorylase a. Both effects result in the inhibition of glycogen mobilization and the formation of glucose from glycogen. Copyright (C) 2000 Elsevier Science Ltd.

A new, scalable preparation of a glucopyranosylidene-spiro- thiohydantoin: One of the best inhibitors of glycogen phosphorylases

Benzobromo-glucose was converted into per-O-benzoylated β-D- glucopyranosyl cyanide by mercury(II) cyanide in nitromethane. Partial hydrolysis of the nitrile with hydrogen bromide in acetic acid gave per-O- benzoylated C-(β-D-glucopyranosyl)formamide. Photobromination using bromine in carbon tetrachloride, chloroform, or dichloromethane gave the corresponding per-O-benzoylated 1-bromo-1-deoxy-β-D-glucopyranosyl cyanide and C-(1-bromo-1-deoxy-β-D-glucopyranosyl)formamide. Reaction of the latter with ammonium thiocyanate in nitromethane gave the per-O-benzoylated C-6S configured glucopyranosylidene-spiro-thiohydantoin together with a small amount of the per-O-benzoylated C-(1-hydroxy-β-D-glucopyranosyl)formamide. Debenzoylation of the spiro-thiohydantoin with sodium methoxide in methanol gave gram amounts of the title inhibitor. The described sequence should be suitable for scaling up and the target compound can be prepared in ~30% overall yield starting from D-glucose. (C) 2000 Elsevier Science Ltd.

Efficient inhibition of muscle and liver glycogen phosphorylases by a new glucopyranosylidene-spiro-thiohydantoin

Reaction of C-(1-bromo-1-deoxy-β-D-glucopyranosyl)formamide 2 with thiocyanate ions was the key step of a short synthesis of D- glucopyranosylidene-spiro-thiohydantoin 7 which proved to be a potent inhibitor of muscle and liver glycogen phosphorylases.