Stereoselective synthesis of both enantiomers of 1,4-anhydro-alditols, 1,4-anhydro-2-amino-alditols and d- and l-isonucleosides from 2,3-O-isopropylidene-d-glyceraldehyde using iodine-induced cyclization as the key step |
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| Institution: | 1. Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China;2. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300171, PR China;1. Namik Kemal University, Muratli Vocational School, Department of Chemical Technology, Muratli, Tekirdag, Turkey;2. Namik Kemal University, Faculty of Science and Arts, Department of Chemistry, 59030 Tekirdag, Turkey;3. Uludag University, Faculty of Science and Arts, Department of Chemistry, 16100 Bursa, Turkey |
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| Abstract: | We have stereoselectively prepared the enantiomeric 1,4-anhydro-alditols (−)-15 and (+)-15, 1,4-anhydro-2-amino-alditols (−)-19 and (+)-19, and isonucleosides (−)-22, (+)-22 and 25, from 2,3-O-isopropylidene-d-glyceraldehyde. The key step was the iodine-induced cyclization of 4-pentene-1,2,3-triols 2 and 3 to give, respectively, the tetrahydrofuran derivatives 4 and 5. In these compounds we have optimized the substitution of iodine for oxygen-bearing groups. Results were best when we used potassium superoxide as a nucleophile. |
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