352541-83-4

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

• 1379002-60-4 (5R,6S,8S,9S)-6-tert-butyldiphenylsilyloxymethyl-8,9-(dimethylmethylenedioxy)-3-phenyl-2-thioxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one 
• 1379002-66-0 3-C-3,5-carbolactono-3-[4-(cyclohex-1-en-1-yl)-1H-1,2,3-triazol-1-yl]-3-deoxy-D-arabinofuranose 
• 1379002-65-9 3-C-3,5-carbolactono-3-[4-(cyclohex-1-en-1-yl)-1H-1,2,3-triazol-1-yl]-3-deoxy-D-arabinofuranose 
• 1379002-59-1 5-O-tert-butyldiphenylsilyl-3-deoxy-3-isothiocyanato-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose 
• 1379002-64-8 3-C-3,5-carbolactono-3-deoxy-3-(4-phenyl-1H-1,2,3-triazol-1-yl)-D-arabinofuranose 
• 1379002-63-7 3-C-3,5-carbolactono-3-deoxy-3-(4-phenyl-1H-1,2,3-triazol-1-yl)-D-arabinofuranose 
• 1379002-89-7 5-O-tert-butyldiphenylsilyl-3-(4-n-butyl-1H-1,2,3-triazol-1-yl)-3-deoxy-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose 
• 1379002-88-6 5-O-tert-butyldiphenylsilyl-3-(4-cyclopentyl-1H-1,2,3-triazol-1-yl)-3-deoxy-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose 
• 1379002-87-5 5-O-tert-butyldiphenylsilyl-3-[4-(cyclohex-1-en-1-yl)-1H-1,2,3-triazol-1-yl]-3-deoxy-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose 
• 1379002-86-4 5-O-tert-butyldiphenylsilyl-3-deoxy-1,2-O-isopropylidene-3-C-methoxycarbonyl-3-(4-phenyl-1H-1,2,3-triazol-1-yl)-β-D-arabinofuranose 
• 1379002-85-3 (5R,6S,8S,9S)-6-tert-butyldiphenylsilyloxymethyl-8,9-(dimethylmethylenedioxy)-3-α-naphthyl-2-selenoxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one 
• 1379002-84-2 (5R,6S,8S,9S)-6-tert-butyldiphenylsilyloxymethyl-8,9-(dimethylmethylenedioxy)-3-p-methylphenyl-2-selenoxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one 
• 1379002-83-1 5-O-tert-butyldiphenylsilyl-3-deoxy-3-isoselenocyanato-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose 
• 1379002-58-0 (3R,4S,6S,7S)-4-tert-butyldiphenylsilyloxymethyl-6,7-(dimethylmethylenedioxy)-5-oxa-1-azaspiro[2.4]heptan-2-one 

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.