Thiamet GDiscontinued

Base Information

• Chemical Name: Thiamet G Discontinued
• CAS No.: 1009816-48-1
• Molecular Formula: C₉H₁₆N₂O₄S
• Molecular Weight: 248.303
• Mol file: 1009816-48-1.mol

Synonyms:Thiamet GDiscontinued;Thiamet G;1,2-Dideoxy-2'-ethylamino-a-D-glucopyranoso-[2,1-d]-2'-thiazoline;2-(ethylaMino)-5-(hydroxyMethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-dio;5H-Pyrano[3,2-d]thiazole-6,7-diol, 2-(ethylamino)-3a,6,7,7a-tetrahydro-5-(hydroxymethyl)-, (3aR,5R,6S,7R,7aR)-;(3aR,5R,6S,7R,7aR)-2-(ethylamino)-3a,6,7,7a-tetrahydro-5-(hydroxymethyl)-5H-Pyrano[3,2-d]thiazole-6,7-diol;(3aR,5R,6S,7R,7aR)-2-(Ethylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol

Chemical Property of Thiamet GDiscontinued

Chemical Property:

• Boiling Point: 483.2±55.0 °C(Predicted)
• PKA: 13.17±0.70(Predicted)
• PSA: 119.61000
• Density: 1.74±0.1 g/cm3(Predicted)
• LogP: -1.66720
• Storage Temp.: ?20°C
• Solubility.: H2O: ≥5mg/mL at warmed to 60°C

Purity/Quality:

99%, ^*data from raw suppliers

Thiamet G ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Thiamet G (1009816-48-1) is a potent, selective inhibitor of O-GlcNAcase (Ki?= 21 nM for human O-GlcNAcase). Increases levels of O-GlcNAc-modified proteins in cellular assays and?in vivo. Suppresses phosphorylation of tau protein in rat cortex and hippocampus.1?Stabilizes tau against aggregation and slows neurodegeneration.2?Thiamet G prevents cognitive decline and amyloid plaque formation in bigenic tau/APP mutant mice.3?Elevates soluble tau species and reduces tauopathy in mouse models.4?Active?in vivo?and blood brain barrier permeable.
• Uses: As a potent O-GlcNAcase inhibitor that blocks phosphorylation of tau in vivo, The authors anticipate that Thiamet-G will find wide use in probing the functional role of O-GlcNAc in vertebrate brain, and it may also offer a route to blocking pathological A potent O-GlcNAcase inhibitor that blocks phosphorylation of tau in vivo. The authors anticipate that Thiamet-G will find wide use in probing the functional role of O-GlcNAc in vertebrate brain, and it may also offer a route to blocking pathological hyperphosphorylation of tau in AD. Anti-Alzheimer''s agent.

Technology Process of Thiamet GDiscontinued

There total 10 articles about Thiamet GDiscontinued which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C14H24N2O6S → (3aR,5R,6S,7S,7aR)-2-(ethylamino)- 5-(hydroxymethyl)-5,6,7,7a- tetrahydro-3aH-pyrano[3,2-d]thiazole- 6,7-diol (1416573-37-9,1009816-48-1)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 3h;

Reference yield:

(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol (1009816-48-1) → (3aR,5R,6S,7S,7aR)-2-(ethylamino)- 5-(hydroxymethyl)-5,6,7,7a- tetrahydro-3aH-pyrano[3,2-d]thiazole- 6,7-diol (1416573-37-9,1009816-48-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N-ethyl-N,N-diisopropylamine / methanol; N,N-dimethyl-formamide / 16 h / 20 °C

2.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 0 - 20 °C

3.1: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / 2 h / -30 - 10 °C / Inert atmosphere

3.2: 20 °C

4.1: potassium carbonate; methanol / 3 h / 20 °C

5.1: hydrogenchloride / methanol / 3 h / 20 °C

With pyridine; hydrogenchloride; methanol; dmap; trifluoromethylsulfonic anhydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

tert-butyl [(3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazol-2-yl]ethylcarbamate (1382799-64-5) → (3aR,5R,6S,7S,7aR)-2-(ethylamino)- 5-(hydroxymethyl)-5,6,7,7a- tetrahydro-3aH-pyrano[3,2-d]thiazole- 6,7-diol (1416573-37-9,1009816-48-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 0 - 20 °C

2.1: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / 2 h / -30 - 10 °C / Inert atmosphere

2.2: 20 °C

3.1: potassium carbonate; methanol / 3 h / 20 °C

4.1: hydrogenchloride / methanol / 3 h / 20 °C

With pyridine; hydrogenchloride; methanol; dmap; trifluoromethylsulfonic anhydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

upstream raw materials:

(2S,3R,4R,5S,6R)-(6-(acetoxymethyl)-3-isothiocyanatotetrahydro-2H-pyran-2,4,5-triyl)triacetate

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride

(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-(3-ethylthioureido)-tetrahydro-2H-pyran-2,4,5-triyl triacetate

tert-butyl [(3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazol-2-yl]ethylcarbamate

Downstream raw materials:

(3aR,5R,6S,7S,7aR)-2-(ethylamino)- 5-(hydroxymethyl)-5,6,7,7a- tetrahydro-3aH-pyrano[3,2-d]thiazole- 6,7-diol

C₃₃H₅₆N₂O₇SSi₂

2-ethylamino-5-[4-(1-hydroxy-1-phenyl-ethyl)-[1,2,3]triazol-1-ylmethyl]-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol

(3aR,5R,6S,7R,7aR)-2-ethylamino-5-((R)-1-hydroxy-3-phenyl-propyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol

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