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- W2040492415 abstract "Abstract The outcome of base-catalysed O- and C-nucleophile additions to the carbonyl group of benzoylated 4-deoxy- d -glycero-hex-3-enopyranosid-2-ulose (1) depends on the conditions used. With methanol/sodium iodide, methanol/sodium methoxide (traces), or methylmagnesium iodide/ether, the addition is followed by benzoyl migration, providing 4-deoxy- d -hexos-3-uloses with an acetal-blocked C-2 carbonyl (8), or a C-2 methyl branch (11). Under more basic conditions in more polar solvents (potassium carbonate/methyl sulfoxide), the addition→acyl migration sequence is preceded by elimination of benzoic acid to give the 4-benzyloxy-2-methoxy-6-methylene-2H-pyran-3-ones of (2S)- (14) and (2R)-configuration (18), from which (S,S)-3-benzoyloxy-2,3-dimethoxy-6-methyldihydropyran-4-one (15) and the enantiomeric (R,R)-analogs 19–21 are obtained in enantiomerically pure form. Each of these carbonyl addition reactions is stereocontrolled by the vicinal anomeric substituent, the nucleophile entering exclusively from the side opposite thereto. Structural and configurational assignments are based on 1H- and 13C-n.m.r. data, on the fact that enantiomers are obtained from enolones epimeric at the anomeric centre (13→15, 9→19), and on an X-ray structural analysis of 19, which adopts a 2S⇌2H3-type conformation with an essentially antiparallel disposition of the newly entered alkoxy group and the anomeric substituent." @default.
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- W2040492415 date "1985-02-01" @default.
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- W2040492415 title "Anomeric stereocontrol in addition reactions to hexose-derived dihydropyranones" @default.
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- W2040492415 doi "https://doi.org/10.1016/0008-6215(85)85182-x" @default.
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