179030-22-9

Basic information

• Product Name: (3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-hydroxyMethyl-2-Methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole
• Synonyms: (3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-hydroxyMethyl-2-Methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole;3a,6,7,7a-Tetrahydro-5-(hydroxyMethyl)-2-Methyl-(3aR,5R,6S,7R,7aR)-5H-pyrano[3,2-d]thiazole-6,7-diol;(3aR,5R,6S,7R,7aR)-5-(Hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;(5R,6S,7R)-5-(Hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;N-Acetyl-glucosaminyl thiazoline
• CAS NO: 179030-22-9
• Molecular Formula: C₈H₁₃NO₄S
• Molecular Weight: 219.25812
• Mol File: 179030-22-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 443.0±45.0 °C(Predicted)
• Appearance: /
• Density: 1.81±0.1 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, Refrigerator, Under inert atmosphere
• Solubility: Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 13.16±0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: (3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-hydroxyMethyl-2-Methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-hydroxyMethyl-2-Methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole(179030-22-9)
• EPA Substance Registry System: (3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-hydroxyMethyl-2-Methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole(179030-22-9)

Safety Data

• Hazardous Substances Data: 179030-22-9(Hazardous Substances Data)

Usage

Description

(3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-hydroxyMethyl-2-Methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole is a complex organic compound with a unique molecular structure. It is characterized by its tetrahydro-pyranothiazole core, which is adorned with multiple hydroxy and hydroxymethyl groups. (3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-hydroxyMethyl-2-Methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole exhibits a high degree of stereoselectivity, as indicated by its detailed stereodescriptors (3aR,5R,6S,7R,7aR). Its structural features make it a promising candidate for various applications in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
(3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-hydroxyMethyl-2-Methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole is used as a key intermediate in the synthesis of Hexosaminidase inhibitors. These inhibitors are emerging drug candidates for the therapy of osteoarthritis, a chronic condition that affects millions of people worldwide. The compound's unique structure allows it to interact with specific biological targets, potentially modulating the activity of enzymes involved in the pathogenesis of osteoarthritis.
Used in Chemical Synthesis:
Due to its complex structure and multiple functional groups, (3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-hydroxyMethyl-2-Methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole can be employed as a versatile building block in the synthesis of various complex organic molecules. Its hydroxy and hydroxymethyl groups can be further modified or functionalized to create a wide range of derivatives with diverse applications in the chemical industry, including the development of new pharmaceuticals, agrochemicals, and specialty chemicals.

Upstream product

• 67145-37-3 (3aR,5R,6S,7R,7aR)-5-(acetoxymethyl)-6,7-diacetoxy-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole 
• 134735-75-4 (S)-3-azido-2-acetamidopropanal diethyl acetal 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 944070-42-2 C₁₆H₁₈F₃NO₈S 

Downstream Products

• 1332868-18-4 C₁₅H₁₉NO₄S 
• 1332868-17-3 C₁₅H₁₉NO₆S₂ 
• 475488-71-2 (3aR,5R,6S,7R,7aR)-5-phenylmethoxymethyl-6,7-bis(phenylmethoxy)-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole 

Relevant articles and documents

NAG-thiazoline, an N-acetyl-β-hexosaminidase inhibitor that implicates acetamido participation

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Combining weak affinity chromatography, NMR spectroscopy and molecular simulations in carbohydrate-lysozyme interaction studies

By examining the interactions between the protein hen egg-white lysozyme (HEWL) and commercially available and chemically synthesized carbohydrate ligands using a combination of weak affinity chromatography (WAC), NMR spectroscopy and molecular simulations, we report on new affinity data as well as a detailed binding model for the HEWL protein. The equilibrium dissociation constants of the ligands were obtained by WAC but also by NMR spectroscopy, which agreed well. The structures of two HEWL-disaccharide complexes in solution were deduced by NMR spectroscopy using 1H saturation transfer difference (STD) effects and transferred 1H,1H-NOESY experiments, relaxation-matrix calculations, molecular docking and molecular dynamics simulations. In solution the two disaccharides β-d-Galp-(1→4) -β-d-GlcpNAc-OMe and β-d-GlcpNAc-(1→4)-β-d-GlcpNAc-OMe bind to the B and C sites of HEWL in a syn-conformation at the glycosidic linkage between the two sugar residues. Intermolecular hydrogen bonding and CH/π-interactions form the basis of the protein-ligand complexes in a way characteristic of carbohydrate-protein interactions. Molecular dynamics simulations with explicit water molecules of both the apo-form of the protein and a ligand-protein complex showed structural change compared to a crystal structure of the protein. The flexibility of HEWL as indicated by a residue-based root-mean-square deviation analysis indicated similarities overall, with some residue specific differences, inter alia, for Arg61 that is situated prior to a flexible loop. The Arg61 flexibility was notably larger in the ligand-complexed form of HEWL. N,N′-Diacetylchitobiose has previously been observed to bind to HEWL at the B and C sites in water solution based on 1H NMR chemical shift changes in the protein whereas the disaccharide binds at either the B and C sites or the C and D sites in different crystal complexes. The present study thus highlights that protein-ligand complexes may vary notably between the solution and solid states, underscoring the importance of targeting the pertinent binding site(s) for inhibition of protein activity and the advantages of combining different techniques in a screening process. The Royal Society of Chemistry 2012.

SELECTIVE GLYCOSIDASE INHIBITORS, METHODS OF MAKING INHIBITORS, AND USES THEREOF

The invention comprises compounds for selectively inhibiting glycosidases, prodrugs of the compounds, and pharmaceutical compositions containing the compounds or prodrugs of the compounds. The invention also comprises animal models and methods of making the animal models for studying diseases and disorders related to deficiency or overexpression of O-GIcNAcase, accumulation or deficiency of O-GIcNAc, and treatment of such diseases and disorders. The invention also comprises methods of treating such diseases and disorders. The invention also comprises methods of making the compounds, and methods of making selective glycosidase inhibitors