Reaction of Glycosyl Halides with Benzyl Grignard Reagents: Unexpected o-Tolyl Alkylation of Tetra-O-acetylglucopyranosyl Bromide and Direct Synthesis of (B-Glycosyl)phenylmethanes
- 1 March 1994
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 13 (2) , 293-302
- https://doi.org/10.1080/07328309408009194
Abstract
The synthesis of (β-glycosyl1)phenylmethanes by Grignard alkylation of glycosyl halides is investigated. Reaction of tetra-O-acetylglucopyranosyl bromide with benzylmagnesium chloride gave a good yield of a 3:1 mixture of 2-(β-d-glucopyranosyl)toluene and (β-glucosyl)phenylmethane. The requirement for an equatorial 2-acetoxy group and 6-acetoxymethyl group for the formation of the unexpected o-tolyl rearrangement product is explored by using xylosyl, mannosyl, and 2-deoxyglucosyl halides as substrates for the alkylation. Synthesis of (β-glucosyl)phenylmethane by alkylation of 2,3,4,6-tetra-O-benzylglucosyl bromide with benzylmagnesium chloride is also presented.Keywords
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