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Homochiral acetals in organic synthesis. A general enantioselective entry to carbohydrate derivatives from non-carbohydrate precursors

✍ Scribed by Eugene A. Mash; Jeffrey B. Arterburn; James A. Fryling


Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
185 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis


Most important was the generality of the separability of diastereomeric @)-methyl lnctyl pyranosides (entries 1,5-9, Table 1) and furanosides (entries 10-12). Note that in entries 5,9,11, and 12, a second stereogenic center in the ring bearing a substituent is stereochemically "linked" t o the chirality at the anomeric center and can thus be resolved by this separation methodology.' However, diastereomeric ketofuranosides 13a and m "fro not chromatographically separable.