benzyl 5-(1-azido-1-deoxy-D-erythro-1,2,3-trihydroxyprop-1-yl)-2-methylfuran-3-carboxylate

Base Information

• Chemical Name: benzyl 5-(1-azido-1-deoxy-D-erythro-1,2,3-trihydroxyprop-1-yl)-2-methylfuran-3-carboxylate
• CAS No.: 906562-65-0
• Molecular Formula: C₁₆H₁₇N₃O₅
• Molecular Weight: 331.328
• Mol file: 906562-65-0.mol

Synonyms:benzyl 5-(1-azido-1-deoxy-D-erythro-1,2,3-trihydroxyprop-1-yl)-2-methylfuran-3-carboxylate

Chemical Property of benzyl 5-(1-azido-1-deoxy-D-erythro-1,2,3-trihydroxyprop-1-yl)-2-methylfuran-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 5-(1-azido-1-deoxy-D-erythro-1,2,3-trihydroxyprop-1-yl)-2-methylfuran-3-carboxylate

There total 7 articles about benzyl 5-(1-azido-1-deoxy-D-erythro-1,2,3-trihydroxyprop-1-yl)-2-methylfuran-3-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: 77.0%

benzyl 5-(3-O-tert-butyldiphenylsilyl-1,2-di-O-sulfinyl-D-threo-1,2,3-trihydroxyprop-1-yl)-2-methylfuran-3-carboxylate (906562-63-8) → benzyl 5-(1-azido-1-deoxy-D-erythro-1,2,3-trihydroxyprop-1-yl)-2-methylfuran-3-carboxylate (906562-65-0)

Guidance literature:

With trimethylsilylazide; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1055/s-2006-941570

Reference yield:

benzyl 5-(3-O-tert-butyldiphenylsilyl-1,2-di-O-sulfinyl-D-erythro-1,2,3-trihydroxyprop-1-yl)-2-methylfuran-3-carboxylate (906562-68-3) → benzyl 5-(1-azido-1-deoxy-D-erythro-1,2,3-trihydroxyprop-1-yl)-2-methylfuran-3-carboxylate (906562-65-0) + benzyl 5-(1-azido-1-deoxy-D-threo-1,2,3-trihydroxyprop-1-yl)-2-methylfuran-3-carboxylate (906562-69-4)

Guidance literature:

With trimethylsilylazide; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 48h; optical yield given as %de;

DOI:10.1002/ejoc.201000183

Reference yield:

benzyl acetoacetate (5396-89-4) → benzyl 5-(1-azido-1-deoxy-D-erythro-1,2,3-trihydroxyprop-1-yl)-2-methylfuran-3-carboxylate (906562-65-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 67 percent / ZnCl₂ / ethanol / 0.5 h / Heating

2: imidazole / dimethylformamide / 0 °C

3: 92 percent / SOCl₂; Et₃N / CH₂Cl₂

4: 77 percent / TMSN₃; TBAF / tetrahydrofuran / 20 °C

With 1H-imidazole; thionyl chloride; trimethylsilylazide; tetrabutyl ammonium fluoride; triethylamine; zinc(II) chloride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-2006-941570

upstream raw materials:

benzyl 5-(3-O-tert-butyldiphenylsilyl-1,2-di-O-sulfinyl-D-threo-1,2,3-trihydroxyprop-1-yl)-2-methylfuran-3-carboxylate

benzyl 5-(3-O-tert-butyldiphenylsilyl-D-threo-1,2,3-trihydroxyprop-1-yl)-2-methylfuran-3-carboxylate

D-xylose

D-Arabinose

Downstream raw materials:

benzyl 5-[(R)-1-azido-2-hydroxyethyl]-2-methylfuran-3-carboxylate

benzyl 5-(1-azido-3-O-tert-butyldiphenylsilyl-1-deoxy-D-erythro-1,2,3-trihydroxyprop-1-yl)-2-methylfuran-3-carboxylate