352541-84-5

Upstream product

• 67-56-1 methanol 
• 352541-83-4 5-O-tert-butyldiphenylsilyl-3-C-trichloromethyl-1,2-O-isopropylidene-β-D-lyxofuranose 
• 114738-04-4 (3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol 
• 172751-32-5 5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-β-D-threo-pentofuranose-3-ulose 

Downstream Products

• 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 
• 1379002-88-6 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 
• 1379002-86-4 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 
• 1379002-61-5 (5R,6S,8S,9S)-6-tert-butyldiphenylsilyloxymethyl-3-cyclohexyl-8,9-(dimethylmethylenedioxy)-2-thioxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one 
• 1379002-71-7 (5R,6S,8S,9S)-8,9-(dimethylmethylenedioxy)-6-hydroxymethyl-3-phenyl-2-thioxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one 
• 1379002-72-8 (5R,6S,8S,9S)-3-cyclohexyl-8,9-(dimethylmethylenedioxy)-6-hydroxymethyl-2-thioxo-7-oxa-1,3-diazaspiro[4.4]nonan-4-one 
• 1379002-74-0 (5R,6S,7R,10S)-6,7,10-trihydroxy-3-phenyl-2-thioxo-8-oxa-1,3-diazaspiro[4.5]decan-4-one 
• 1379002-73-9 (5R,6S,7S,10S)-6,7,10-trihydroxy-3-phenyl-2-thioxo-8-oxa-1,3-diazaspiro[4.5]decan-4-one 
• 1379002-58-0 (3R,4S,6S,7S)-4-tert-butyldiphenylsilyloxymethyl-6,7-(dimethylmethylenedioxy)-5-oxa-1-azaspiro[2.4]heptan-2-one 
• 1379002-57-9 3-amino-3-deoxy-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose 
• 1379002-77-3 (5R,6S,7R,10S)-3-cyclohexyl-6,7,10-trihydroxy-2-thioxo-8-oxa-1,3-diazaspiro[4.5]decan-4-one 
• 1379002-79-5 (5R,6S,7S,10S)-3-cyclohexyl-6,7,10-trihydroxy-2-thioxo-8-oxa-1,3-diazaspiro[4.5]decan-4-one 
• 1379002-82-0 5-O-tert-butyldiphenylsilyl-3-deoxy-3-formamido-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 

Relevant academic research and scientific papers

Synthesis of conformationally-constrained thio(seleno)hydantoins and α-triazolyl lactones from d-arabinose as potential glycosidase inhibitors

We have explored the rich structural diversity provided by an α-azido ester derived from d-arabinose as the source of sugar templates with reduced conformational flexibility. Using transient α-thioureido(selenoureido) esters we have prepared spiranic thio(seleno)hydantoins at the C-3 position of the sugar moiety. In this context, the first example of a stable spiranic α-lactam (or aziridinone) was isolated as a by-product in the hydrogenolysis of the starting α-azido ester. Furthermore, using copper(I)-catalyzed azido-alkyne cycloaddition (click chemistry), we have accessed bicyclic cis-fused α-triazolyl lactones fixed in the furanose form. Spiranic thiohydantoins turned out to be moderate, though selective, inhibitors of glycosidases, whereas their selenium isosters behaved as good free radical scavengers.

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.