189633-62-3

Usage

Uses

Used in Pharmaceutical Applications:
(2R,3R,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 agent for its potential therapeutic properties. (2R,3R,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 may contribute to its efficacy in treating specific medical conditions, although further research is needed to determine its exact applications and mechanisms of action.
Used in Biochemical Research:
In the field of biochemistry, (2R,3R,4S,5R,6S)-3,4,6-TRIHYDROXY-2-HYDROXYMETHYL-7,9-DIAZA-1-OXA-SPIRO[4,5]DECANE-10-ONE-8-THIONE can be utilized as a research tool to study the interactions between biomolecules and macromolecules. Its hydroxyl and thione groups may facilitate binding and other biochemical processes, providing valuable insights into the compound's role in biological systems.
Used in Materials Science:
(2R,3R,4S,5R,6S)-3,4,6-TRIHYDROXY-2-HYDROXYMETHYL-7,9-DIAZA-1-OXA-SPIRO[4,5]DECANE-10-ONE-8-THIONE may also find applications in materials science, where its distinct structural features could be harnessed to develop new materials with unique properties. (2R,3R,4S,5R,6S)-3,4,6-TRIHYDROXY-2-HYDROXYMETHYL-7,9-DIAZA-1-OXA-SPIRO[4,5]DECANE-10-ONE-8-THIONE's potential use in this field would depend on its stability, reactivity, and compatibility with other materials, which would require further investigation and experimentation.

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

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.

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

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.