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4143110833
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note
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The reaction of mannose derivative 7 with BzCl was also tried. The desired monobenzoylated product was too unstable to purify by column chromatography. The benzoyl group migrated from one hydroxyl to another hydroxyl position during standing and separation process, and we finally got the mixture of 2- and 3-benzoylated product in a ratio of ∼1:1.
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4143107472
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note
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In contrast, we treated methyl 4,6-O-benzylidene-β-D-glucopyranoside (4) with TsCl and pyridine, the 3-tosylated product was isolated in 48% yield as the major product.
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4143066394
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note
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Using ethyl acetate, toluene, or 1,2-dichloroethane as solvent, similar results (yields and product ratios) were also obtained. Because 1,2-dichloroethane is more toxic and the solubility of saccharides in ethyl acetate or toluene is not good, we eventually chose dichloromethane as the solvent to perform the reaction.
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Marshall, J.A.1
Seletsky, B.M.2
Luke, G.P.3
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