- 1,6-Anhydrofuanoses, XIV. - Selective Monotosylation of 1,6-Anhydro-β-D-mannofuranose
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Monotosylation of 1,6-anhydro-β-D-mannofuranose (1) with p-toluenesulfonyl chloride in pyridine gives the 5-O-tosylate 2a in high yield (79percent).As by-products of the reaction small amounts of the 3-O-monotosylate 3a (0.4percent) as well as the 2,5- and 3,5-di-O-tosylates 4a (3.5percent) and 5a (1.2percent), respectively, are isolated.Product identification was achieved by 1H NMR spectroscopy in comparison with the data for the acetates 2b, 3b, 4b, and 5b.Observed selectivities are rationalized by concerning steric and electronic effects.
- Koell, Peter,Komander, Herbert,Meyer, Bernd,Lendering, Ursula
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p. 1591 - 1596
(2007/10/02)
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