Selective replacement of primary hydroxyl groups in carbohydrates: preparation of some carbohydrate derivatives containing halomethyl groups |
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Authors: | Abul Kashem M. Anisuzzaman Roy L. Whistler |
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Affiliation: | Department of Biochemistry, Purdue University, West Lafayette, Indiana 47907 U.S.A. |
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Abstract: | Selective halogenation of hydroxymethyl groups in sugars and nucleosides has been achieved by use of triphenylphosphine and carbon tetrahalides (chloride, bromide, or iodide) in pyridine. Methyl α-d-glucopyranoside, 1,2,-O-isopropylidene-α-d-glucofuranose, inosine, and uridine give almost quantitative yields of their primary halomethyl analogs. Similarly, 6,6′-dichloro-6,6′-dideoxysucrose is prepared from sucrose. Chlorination and bromination of 5,6-anhydro-1,2-O-isopropylidene-α-d-glucofuranose by these reagents give 6-chloro-6-deoxy-1,2-O-isopropylidene-α-d-glucofuranose and 6-bromo-6-deoxy-1,2-O-iso-propylidene-α-d-glucofuranose, respectively. |
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