1-α-[2',3'-di-O-acetyl-5'-(tert-butyldiphenylsilyl)-D-arabinofuranosyl]-2-nitroimidazole

Base Information

• Chemical Name: 1-α-[2',3'-di-O-acetyl-5'-(tert-butyldiphenylsilyl)-D-arabinofuranosyl]-2-nitroimidazole
• CAS No.: 220792-97-2
• Molecular Formula: C₂₈H₃₃N₃O₈Si
• Molecular Weight: 567.671

Synonyms:1-α-[2',3'-di-O-acetyl-5'-(tert-butyldiphenylsilyl)-D-arabinofuranosyl]-2-nitroimidazole

Chemical Property of 1-α-[2',3'-di-O-acetyl-5'-(tert-butyldiphenylsilyl)-D-arabinofuranosyl]-2-nitroimidazole

Chemical Property:

Purity/Quality:

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Technology Process of 1-α-[2',3'-di-O-acetyl-5'-(tert-butyldiphenylsilyl)-D-arabinofuranosyl]-2-nitroimidazole

There total 4 articles about 1-α-[2',3'-di-O-acetyl-5'-(tert-butyldiphenylsilyl)-D-arabinofuranosyl]-2-nitroimidazole 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: 72.0%

1,2,3-tri-O-acetyl-5-O-t-butyldiphenylsilyl-D-arabinofuranose (845868-93-1) + 2-nitro-1-(triethylsilyl)imidazole → 1-α-[2',3'-di-O-acetyl-5'-(tert-butyldiphenylsilyl)-D-arabinofuranosyl]-2-nitroimidazole (220792-97-2)

Guidance literature:

1,2,3-tri-O-acetyl-5-O-t-butyldiphenylsilyl-D-arabinofuranose; 2-nitro-1-(triethylsilyl)imidazole; In acetonitrile; at -20 ℃; Inert atmosphere;

With triethylsilyl trifluoromethyl sulfonate; In 1,2-dichloro-ethane; acetonitrile; at -8 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jo200727k

Reference yield: 16.0%

1,2,3-tri-O-acetyl-5-O-t-butyldiphenylsilyl-D-arabinofuranose (845868-93-1) + 2-nitro-1-(triethylsilyl)imidazole → 1-α-[2',3'-di-O-acetyl-5'-(tert-butyldiphenylsilyl)-D-arabinofuranosyl]-2-nitroimidazole (220792-97-2) + 1-β-[2',3'-di-O-acetyl-5'-(tert-butyldiphenylsilyl)-D-arabinofuranosyl]-2-nitroimidazole (639079-80-4)

Guidance literature:

1,2,3-tri-O-acetyl-5-O-t-butyldiphenylsilyl-D-arabinofuranose; 2-nitro-1-(triethylsilyl)imidazole; In 1,2-dichloro-ethane; at 20 ℃; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/jo200727k

Reference yield:

acetic anhydride (108-24-7) + (2R,3S,4S,5S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-(2-nitro-imidazol-1-yl)-tetrahydro-furan-3,4-diol → 1-α-[2',3'-di-O-acetyl-5'-(tert-butyldiphenylsilyl)-D-arabinofuranosyl]-2-nitroimidazole (220792-97-2)

Guidance literature:

With pyridine; for 4h;

DOI:10.1002/(SICI)1099-1344(199901)42:1<3::AID-JLCR160>3.0.CO;2-H

upstream raw materials:

acetic anhydride

tert-butylchlorodiphenylsilane

1,2,3-tri-O-acetyl-5-O-t-butyldiphenylsilyl-D-arabinofuranose

Downstream raw materials:

fluoroazomycin arabinoside

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