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Iodine Promoted Glycosylation with Glycosyl Iodides: a-Glycoside Synthesis

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TextSeries: ; Journal of Carbohydrate Chemistry, 24, p.463-474, 2005Contained works:

Van Well, R.M
Ravindranathan, K.P
Field, R.A

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Abstract: Glycosidation of fully acetylated glucopyranosyl iodide with methanol under the influence of iodine gave a-glucoside selectively. Use of less reactive acceptors led to the formation of a/b-mixtures. Glycosylations with fully benzoylated glucosyl iodide yielded b-glucosides only. In contrast, iodine-promoted glycosylation of serine and threonine with 2-azido-2-deoxy-glycosyl iodides, easily obtained in three steps, proceeded smoothly, resulting in only a-linked products in high yield in most cases.

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Glycosidation of fully acetylated glucopyranosyl iodide with methanol under the influence of iodine gave a-glucoside selectively. Use of less reactive acceptors led to the formation of a/b-mixtures. Glycosylations with fully benzoylated glucosyl iodide yielded b-glucosides only. In contrast, iodine-promoted glycosylation of serine and threonine with 2-azido-2-deoxy-glycosyl iodides, easily obtained in three steps, proceeded smoothly, resulting in only a-linked products in high yield in most cases.

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