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- W2096291298 abstract "The regioselectivity of electrophilic additions of the C=C double bond in 7-oxabicyclo[2.2.1]hept-5-en-2-yl (7-oxanorborn-5-en-2-yl) derivatives depends on the nature of the substituents at C(2). The adducts so-obtained can be transformed into the corresponding 5,6-disubstituted 7-oxanorbornan-2-ones, which can be monosubstituted at C(3) stereoselectively, giving products with the same stereochemical information as hexoses. Thus, optically pure 7-oxanorborn-5-en-2-yl derivatives can be viewed as naked sugars Applications to the total, asymmetric syntheses of L-daunosamine, 2-deoxy-L-fucose, D- and L-allose, D- and L-talose, D- and L-ribose, D- and L-methyl 2,5-anhydroallonate, cyclohexenepolyols, (4R,5R,6R)-2-crotonyloxymethyl-4,5,6-trihydroxycyclohex-2-enone, (+)- and (-)-methyl nonactate are presented." @default.
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- W2096291298 date "1989-12-30" @default.
- W2096291298 modified "2023-10-09" @default.
- W2096291298 title "Synthesis of Carbohydrates and Derivatives from 7-Oxanorbornenes (Naked Sugars)" @default.
- W2096291298 doi "https://doi.org/10.1021/bk-1989-0386.ch013" @default.
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