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

Base Information

• Chemical Name: benzyl 5-(3-O-tert-butyldiphenylsilyl-1,2-di-O-sulfinyl-D-threo-1,2,3-trihydroxyprop-1-yl)-2-methylfuran-3-carboxylate
• CAS No.: 906562-63-8
• Molecular Formula: C₃₂H₃₄O₇SSi
• Molecular Weight: 590.769
• Mol file: 906562-63-8.mol

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

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

There total 5 articles about benzyl 5-(3-O-tert-butyldiphenylsilyl-1,2-di-O-sulfinyl-D-threo-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: 92.0%

benzyl 5-(3-O-tert-butyldiphenylsilyl-D-threo-1,2,3-trihydroxyprop-1-yl)-2-methylfuran-3-carboxylate (906562-62-7) → 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)

Guidance literature:

With thionyl chloride; triethylamine; In dichloromethane;

DOI:10.1055/s-2006-941570

Reference yield:

benzyl acetoacetate (5396-89-4) → 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)

Guidance literature:

Multi-step reaction with 3 steps

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

2: imidazole / dimethylformamide / 0 °C

3: 92 percent / SOCl₂; Et₃N / CH₂Cl₂

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

DOI:10.1055/s-2006-941570

Reference yield:

2-methyl-5-(1,2,3-trihydroxy-propyl)-furan-3-carboxylic acid benzyl ester → 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)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 0 °C

2: 92 percent / SOCl₂; Et₃N / CH₂Cl₂

With 1H-imidazole; thionyl chloride; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-2006-941570

upstream raw materials:

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

D-xylose

D-Arabinose

benzyl acetoacetate

Downstream raw materials:

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

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

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