548448-70-0

Basic information

• Product Name: (Z)-6-O-(tert-butyldimethylsilyl)-1-(4,5-dichloro-2-nitrophenyl)-1,2-dideoxy-3,4-O-isopropylidene-D-allo-1-enitol
• Synonyms: (Z)-6-O-(tert-butyldimethylsilyl)-1-(4,5-dichloro-2-nitrophenyl)-1,2-dideoxy-3,4-O-isopropylidene-D-allo-1-enitol
• CAS NO: 548448-70-0
• Molecular Weight: 492.472
• Mol File: 548448-70-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (Z)-6-O-(tert-butyldimethylsilyl)-1-(4,5-dichloro-2-nitrophenyl)-1,2-dideoxy-3,4-O-isopropylidene-D-allo-1-enitol(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-6-O-(tert-butyldimethylsilyl)-1-(4,5-dichloro-2-nitrophenyl)-1,2-dideoxy-3,4-O-isopropylidene-D-allo-1-enitol(548448-70-0)
• EPA Substance Registry System: (Z)-6-O-(tert-butyldimethylsilyl)-1-(4,5-dichloro-2-nitrophenyl)-1,2-dideoxy-3,4-O-isopropylidene-D-allo-1-enitol(548448-70-0)

Safety Data

• Hazardous Substances Data: 548448-70-0(Hazardous Substances Data)

Upstream product

• 93213-80-0 4,5-dichloro-2-nitrobenzyl bromide 
• 7494-45-3 1,2-dichloro-4-methyl-5-nitrobenzene 
• 217309-46-1 5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose 
• 548448-68-6 (4,5-dichloro-2-nitrobenzyl)triphenylphosphorane 

Relevant articles and documents

Convergent synthesis of polyhalogenated quinoline C-nucleosides as potential antiviral agents

2,5,6-Trichloro-1-(β-D-ribofuranosyl)benzimidazole (TCRB) and 2-bromo-5,6-dichloro-1-(β-D-ribofuranosyl)benzimidazole (BDCRB) are benzimidazole nucleosides that exhibit strong and selective anti-HCMV activity. We proposed to synthesize 2-halo-6,7-dichloro-4-(β-D-ribofuranosyl)quinolines as 6 + 6 bicyclic analogues of TCRB. The synthesis used Wittig reactions in two key steps. The first Wittig reaction coupled a fully functionalized benzene with a ribofuranose derivative to provide (Z)-6-O-(tert-butyldimethylsilyl)-1-(4,5-dichloro-2-nitrophenyl)- 1,2-dideoxy-3,4-O-isopropylideneD-allo-1-enitol (5) as the basic skeleton for the target compounds. The following electrophile-mediated intramolecular cyclization of the cis-alkene (5) was found to afford (1S,2S)-2,5-anhydro-1-bromo6-O-(tert-butyldimethylsilyl)- 1-deoxy-1-(4,5-dichloro-2-nitrophenyl)-3,4-O-isopropylidene-D-allitol (8) as the major product. This α-stereoselectivity was contrary to the literature precedence. A doublebond isomerization was established to be the cause of the unexpected stereochemistry. The bromo group of 8 was displaced by a hydroxyl group. Oxidation of the hydroxy group and the reduction of a phenylnitro group provided (2S)-1-(2-amino-4,5-dichlorophenyl)-2,5-anhydro-6-O- (tert-butyldimethylsilyl)-3,4-O-isopropylidene-D-allose (11), which was subjected to the second Wittig reaction with a phosphacumulene to construct 4-[5-O -(tert-butyldimethylsilyl)-2,3-O- isopropylidene-α-Dribofuranosyl]-6,7-dichloroquinolin-2-one (13). Halogenation followed by deprotection of 13 and led to the synthesis of 4-(α -D-ribofuranosyl)-2,6,7-trichloroquinoline (17) as the major product. The 2-aminophenone α-nucleoside (11) was successfully anomerized to the β-anomer (19), which led to the synthesis of the targeted 2-chloro- and 2-bromo-6,7-dichloro-4-(β-D-ribofuranosyl)quinolines (18 and 21, respectively).