Stereospecific fluorination of 1,3,5-tri-O-benzoyl-α-D-ribofuranose-2-sulfonate esters: Preparation of a versatile intermediate for synthesis of 2′-[ (18)F ]-fluoro-arabinonucleosides Journal Article
| Authors: | Alauddin, M. M.; Conti, P. S.; Mathew, T.; Fissekis, J. D.; Surya Prakash, G. K.; Watanabe, K. A. |
| Article Title: | Stereospecific fluorination of 1,3,5-tri-O-benzoyl-α-D-ribofuranose-2-sulfonate esters: Preparation of a versatile intermediate for synthesis of 2′-[ (18)F ]-fluoro-arabinonucleosides |
| Abstract: | A detailed investigation on fluorination of 1,3,5-tri-O-benzoyl-α-D-ribofuranose-2-sulphonate esters is reported. Various combinations of sulfonate esters, fluorinating agents and solvents were evaluated in this study. Organic ammonium fluoride, in particular n-Bu4NF, was found to be better fluorinating agent than inorganic fluoride, and 1,3,5-tri-O-benzoyl-α-D-ribofuranose-2-trifluoromethylsulphonate ester appeared to be the best substrate. The developed method is suitable for stereospecific (arabino) incorporation of radiofluorine (18F) into the sugar moiety. © 2000 Elsevier Science S.A. |
| Keywords: | fluorination; n-bu4nf; nucleophilic radiofluorine |
| Journal Title: | Journal of Fluorine Chemistry |
| Volume: | 106 |
| Issue: | 1 |
| ISSN: | 0022-1139 |
| Publisher: | Elsevier Science, Inc. |
| Date Published: | 2000-10-01 |
| Start Page: | 87 |
| End Page: | 91 |
| Language: | English |
| PROVIDER: | scopus |
| DOI: | 10.1016/S0022-1139(00)00307-9 |
| DOI/URL: | |
| Notes: | Export Date: 18 November 2015 -- Source: Scopus |
