The reaction of carbohydrates with triphenyl phosphite methiodide and related compounds : A new synthesis of deoxysugars |
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Affiliation: | 1. Doctor Degree Program in Marine Biotechnology, National Sun Yat-sen University/Academia Sinica, Kaohsiung 80424, Taiwan;2. Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 80424, Taiwan;3. Department of Biomedical Science and Environmental Biology, Kaohsiung Medical University, Kaohsiung 80708, Taiwan;4. Institute of Biological Chemistry, Academia Sinica, Taipei 11524, Taiwan;5. Institute of Medical Science and Technology, National Sun Yat-sen University, Kaohsiung 80424, Taiwan;6. Department of Medical Research, China Medical University Hospital, China Medical University, Taichung 40402, Taiwan;7. Cancer Center, Kaohsiung Medical University Hospital, Kaohsiung Medical University, Kaohsiung 80708, Taiwan;8. Center for Research Resources and Development of Kaohsiung Medical University, Kaohsiung 80708, Taiwan;1. School of Materials Science and Engineering, Tianjin University, Tianjin, 300072, PR China;2. State Key Laboratory of Electroanalytical Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, PR China;3. University of Chinese Academy of Sciences, Beijing, 100049, PR China |
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Abstract: | Triphenyl phosphite methiodide and related compounds are proposed as reagents for replacing hydroxyls of protected carbohydrates by halogen atoms. The ease of the substitution reaction depends on steric accessibility of the hydroxyl to an SN2 attack. Isopropylidene and benzylidene as well as ester protective groupings can migrate under the reaction conditions; possible mechanisms of these migrations are discussed. As a result, a new route to deoxysugars starting from partially methylated or tosylated monosaccharides has been developed. |
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