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

Base Information

• Chemical Name: ethyl 2-(5-O-benzoyl-2-decanamido-2-deoxy-β-D-ribofuranosyl)thiazole-4-carboxylate
• CAS No.: 1332330-10-5
• Molecular Formula: C₂₈H₃₈N₂O₇S
• Molecular Weight: 546.685
• Mol file: 1332330-10-5.mol

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

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

There total 8 articles about ethyl 2-(5-O-benzoyl-2-decanamido-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: 47.0%

ethyl Bromopyruvate (70-23-5) + 2,5-anhydro-6-O-benzoyl-3-decanamido-3-deoxy-D-allonothioamide (1332330-08-1) → ethyl 2-(5-O-benzoyl-2-decanamido-2-deoxy-β-D-ribofuranosyl)thiazole-4-carboxylate (1332330-10-5)

Guidance literature:

In ethanol; for 0.833333h; Reflux;

DOI:10.1016/j.tet.2011.06.090

Reference yield:

2,5-anhydro-6-O-benzoyl-4-O-decanoyl-3-O-methanesulfonyl-D-glucose ethylene acetal (1332330-01-4) → ethyl 2-(5-O-benzoyl-2-decanamido-2-deoxy-β-D-ribofuranosyl)thiazole-4-carboxylate (1332330-10-5)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium azide / dimethyl sulfoxide / 27 h / 110 °C

2: hydrogenchloride; water; trifluoroacetic acid / 216 h / 4 °C

3: hydroxylamine hydrochloride; sodium acetate / ethanol; dichloromethane / 2 h / 20 °C

4: pyridine; methanesulfonyl chloride / 2.75 h / -15 - 20 °C

5: pyridine; hydrogen sulfide / 96 h / 20 °C

6: ethanol / 0.83 h / Reflux

With pyridine; hydrogenchloride; sodium azide; hydrogen sulfide; hydroxylamine hydrochloride; water; sodium acetate; methanesulfonyl chloride; trifluoroacetic acid; In ethanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/j.tet.2011.06.090

Reference yield:

2,5-anhydro-3-azido-6-O-benzoyl-4-O-decanoyl-3-deoxy-D-allose ethylene acetal (1332330-03-6) → ethyl 2-(5-O-benzoyl-2-decanamido-2-deoxy-β-D-ribofuranosyl)thiazole-4-carboxylate (1332330-10-5)

Guidance literature:

Multi-step reaction with 5 steps

1: hydrogenchloride; water; trifluoroacetic acid / 216 h / 4 °C

2: hydroxylamine hydrochloride; sodium acetate / ethanol; dichloromethane / 2 h / 20 °C

3: pyridine; methanesulfonyl chloride / 2.75 h / -15 - 20 °C

4: pyridine; hydrogen sulfide / 96 h / 20 °C

5: ethanol / 0.83 h / Reflux

With pyridine; hydrogenchloride; hydrogen sulfide; hydroxylamine hydrochloride; water; sodium acetate; methanesulfonyl chloride; trifluoroacetic acid; In ethanol; dichloromethane;

DOI:10.1016/j.tet.2011.06.090

upstream raw materials:

2,5-anhydro-6-O-benzoyl-4-O-decanoyl-3-O-methanesulfonyl-D-glucose ethylene acetal

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

2,5-anhydro-3-azido-6-O-benzoyl-4-O-decanoyl-3-deoxy-D-allononitrile

ethyl Bromopyruvate