352541-96-9

Upstream product

• 114738-04-4 (3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol 

Downstream Products

• 352542-12-2 1-(3-C-azido-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-α-D-arabinofuranosyl)thymine 
• 352542-10-0 1-(3-C-azido-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-β-D-arabinofuranosyl)thymine 
• 352542-16-6 (1S,2S,4S,5S)-1-azido-2-(p-methoxyphenoxy)methyl-4-(thymin-1-yl)-3,6-dioxabicyclo[3.2.0]heptane 
• 352542-14-4 (1R,2S,4R,5S)-1-azido-2-(p-methoxyphenoxy)methyl-4-(thymin-1-yl)-3,6-dioxabicyclo[3.2.0]heptane 
• 352542-06-4 3-C-azido-1,2-O-isopropylidene-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-β-D-arabinofuranose 
• 352542-08-6 methyl 3-C-azido-3-C-methanesulfonyloxymethyl-5-O-p-methoxyphenyl-D-arabinofuranoside 
• 352542-00-8 1,2-O-isopropylidene-5-O-p-methoxyphenyl-3-C-trichloromethyl-β-D-lyxofuranose 
• 352542-02-0 3-C-azido-1,2-O-isopropylidene-3-C-methoxycarbonyl-5-O-p-methoxyphenyl-β-D-arabinofuranose 
• 352542-04-2 3-C-azido-1,2-O-isopropylidene-3-C-hydroxymethyl-5-O-p-methoxyphenyl-β-D-arabinofuranose 
• 352541-98-1 1,2-O-isopropylidene-5-O-p-methoxyphenyl-β-D-arabinofuran-3-ulose 

Relevant academic research and scientific papers

Synthesis of a bicyclic analogue of AZT restricted in an unusual O4′-endo conformation

The [3.2.0]bicyclic β-nucleoside analogue 5 has been designed as a conformationally restricted analogue of the anti-HIV drug AZT. The synthesis of 5 as well as its α-anomer 29 is hereby described. The synthesis was accomplished from D-arabinose via a modified Corey-Link procedure stereo-selectively incorporating the azide moiety as well as a methyl ester function. When the tertbutyldiphenylsilyl group was used as a permanent protecting group, a selective formation of an oxetane ring failed. When using the p-methoxyphenyl group as a permanent protecting group, 5 and 29 were efficiently obtained via a selective reduction of the ester, a nucleobase coupling followed by separation of the anomers and ring-closing procedures. The nucleoside 5 is conformationally restricted in an unusual O4′-endo (East) conformation, which is an intermediate between the North- and South-type conformations. Nevertheless, neither 5 nor 29 displayed any anti-HIV activity.