ethyl 2-(2-benzamido-5-O-benzoyl-2-deoxy-β-D-ribofuranosyl)thiazole-4-carboxylate

Base Information

• Chemical Name: ethyl 2-(2-benzamido-5-O-benzoyl-2-deoxy-β-D-ribofuranosyl)thiazole-4-carboxylate
• CAS No.: 781642-74-8
• Molecular Formula: C₂₅H₂₄N₂O₇S
• Molecular Weight: 496.541
• Mol file: 781642-74-8.mol

Synonyms:ethyl 2-(2-benzamido-5-O-benzoyl-2-deoxy-β-D-ribofuranosyl)thiazole-4-carboxylate

Chemical Property of ethyl 2-(2-benzamido-5-O-benzoyl-2-deoxy-β-D-ribofuranosyl)thiazole-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-(2-benzamido-5-O-benzoyl-2-deoxy-β-D-ribofuranosyl)thiazole-4-carboxylate

There total 7 articles about ethyl 2-(2-benzamido-5-O-benzoyl-2-deoxy-β-D-ribofuranosyl)thiazole-4-carboxylate 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: 55.0%

ethyl Bromopyruvate (70-23-5) + 2,5-anhydro-3-benzamido-6-O-benzoyl-3-deoxy-D-allonothioamide (781642-69-1) → ethyl 2-(2-benzamido-5-O-benzoyl-2-deoxy-β-D-ribofuranosyl)thiazole-4-carboxylate (781642-74-8)

Guidance literature:

In ethanol; for 1.33333h; Heating;

DOI:10.1016/j.tetlet.2004.07.104

Reference yield:

C20H18N4O6 → ethyl 2-(2-benzamido-5-O-benzoyl-2-deoxy-β-D-ribofuranosyl)thiazole-4-carboxylate (781642-74-8)

Guidance literature:

Multi-step reaction with 3 steps

1: MsCl; pyridine / 2.5 h / -15 - 20 °C

2: 82 percent / H₂S; DMAP / ethanol / 8 h / 20 °C

3: 55 percent / ethanol / 1.33 h / Heating

With pyridine; dmap; hydrogen sulfide; methanesulfonyl chloride; In ethanol;

DOI:10.1016/j.tetlet.2004.07.104

Reference yield:

C20H17N3O6 → ethyl 2-(2-benzamido-5-O-benzoyl-2-deoxy-β-D-ribofuranosyl)thiazole-4-carboxylate (781642-74-8)

Guidance literature:

Multi-step reaction with 4 steps

1: NH₂OH*HCl; NaOAc / ethanol; CH₂Cl₂ / 2 h / 20 °C

2: MsCl; pyridine / 2.5 h / -15 - 20 °C

3: 82 percent / H₂S; DMAP / ethanol / 8 h / 20 °C

4: 55 percent / ethanol / 1.33 h / Heating

With pyridine; dmap; hydrogen sulfide; hydroxylamine hydrochloride; sodium acetate; methanesulfonyl chloride; In ethanol; dichloromethane;

DOI:10.1016/j.tetlet.2004.07.104

upstream raw materials:

ethyl Bromopyruvate

2,5-anhydro-3-benzamido-6-O-benzoyl-3-deoxy-D-allonothioamide

2,5-anhydro-3-azido-6-O-benzoyl-4-O-benzyl-3-deoxy-D-allose ethylene acetal

Benzoic acid (2R,3S,4R,5R)-4-azido-5-[1,3]dioxolan-2-yl-3-hydroxy-tetrahydro-furan-2-ylmethyl ester