2beta-Xylofuranosylthiazole-4-carboxamide

Base Information

• Chemical Name: 2beta-Xylofuranosylthiazole-4-carboxamide
• CAS No.: 92952-40-4
• Molecular Formula: C₉H₁₂N₂O₅S
• Molecular Weight: 260.271
• ChEMBL ID: CHEMBL2158240
• Mol file: 92952-40-4.mol

Synonyms:2-beta-xylofuranosylthiazole-4-carboxamide;Xylo-T

Chemical Property of 2beta-Xylofuranosylthiazole-4-carboxamide

Chemical Property:

• Vapor Pressure: 2.53E-17mmHg at 25°C
• Boiling Point: 641.3°Cat760mmHg
• Flash Point: 341.6°C
• PSA: 154.14000
• Density: 1.648g/cm³
• LogP: -0.90370
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 260.04669266
• Heavy Atom Count: 17
• Complexity: 305

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(N=C(S1)C2C(C(C(O2)CO)O)O)C(=O)N
• Isomeric SMILES: C1=C(N=C(S1)[C@H]2[C@@H]([C@H]([C@H](O2)CO)O)O)C(=O)N

Technology Process of 2beta-Xylofuranosylthiazole-4-carboxamide

There total 9 articles about 2beta-Xylofuranosylthiazole-4-carboxamide 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: 89.0%

ethyl 2-(2,3,5-tri-O-benzoyl-β-D-xylofuranosyl)thiazole-4-carboxylate → 2-(β-D-xylofuranosyl)thiazole-4-carboxamide (92952-40-4)

Guidance literature:

With ammonia; In methanol; at 20 ℃;

DOI:10.1016/j.ejmech.2019.111712

Reference yield: 89.0%

C27H25NO9S (1409941-12-3) → 2-(β-D-xylofuranosyl)thiazole-4-carboxamide (92952-40-4)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 144h;

DOI:10.1016/j.bmcl.2012.08.093

Reference yield:

tiazofurin (60084-10-8) → 2-(β-D-xylofuranosyl)thiazole-4-carboxamide (92952-40-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 78 percent / 3 h / Temperature: from -20 deg C to room temp.

2: pyridinium p-toluenesulfonate / CH₂Cl₂ / 24 h / Ambient temperature

3: HF*Pyr / tetrahydrofuran / 24 h / Ambient temperature

4: 4 h / Ambient temperature

5: 70 percent / pyridine; CH₂Cl₂ / 4 h / Temperature: from -20 deg C to 0 deg C

6: 97 percent / hexamethylphosphoric acid triamide; dimethylformamide / 20 h / Ambient temperature

7: 1.) NH₃, 2.) aq. acetic acid / 1.) methanol, room temp., 2.) room temp.

With ammonia; pyridinium p-toluenesulfonate; pyridine hydrogenfluoride; acetic acid; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)81174-6

upstream raw materials:

Acetic acid (2R,3S,4R,5R)-5-(4-carbamoyl-thiazol-2-yl)-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-3-yl ester

tiazofurin

2-[(2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yl]-thiazole-4-carboxylic acid amide

3',5'-O-(1,1,3,3-tetraisopropyldisilox-1,3-diyl)tiazofurin