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- W2949803873 abstract "Abstract Preparative routes for anomerically specific 1- C -allylation of 2-amino-2-deoxy sugars have been evaluated in a comparative study of various N -substituents and aglycons as precursors for glycosyl radicals that effectively capture an allyl group from allyltributyltin. The crystalline triacetate 4 of 3-(2-acetamido-2-deoxy- α - d -glucopyranosyl)-1-propene ( 6 ) was obtained in 70% yield when 2-acetamido-3,4,6-tri- O -acetyl-2-deoxy- α - d -glucopyranosyl chloride ( 1 ) was treated with allyltributyltin under free-radical conditions, whereas the corresponding bromide 3 led only to an oxazolidine derivative; the β -1-ethylxanthate analogue of 1 gave 4 , but in only 25% yield. The 2-trifluoroacetamido 1-bromide analogue of 1 was also an effective radical source, giving the 2-trifluoroacetamido analogue 8 of 4 in 60% yield. The free amino analogue 7 of 4 was conveniently obtained via the 2- p -methoxybenzylideneamino 1-bromide analogue of 1 . Use of 3,4,6-tri- O -acetyl-2-deoxy-2-phthalimido- β - d -glucopyranosyl bromide as radical precursor allowed stereospecific access to β -1- C -allyl derivatives of the amino sugar. The crystalline galactosamine analogue 12 of 4 was obtained by using the galacto analogue of chloride 1 , but the corresponding manno chloride gave only an oxazoline product. The 1- C -allylated amino sugar derivatives are conformationally more mobile than derivatives not having a 1- C -linked substituent." @default.
- W2949803873 created "2019-06-27" @default.
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- W2949803873 date "2010-06-18" @default.
- W2949803873 modified "2023-09-27" @default.
- W2949803873 title "ChemInform Abstract: Stereocontrolled Allylation of 2-Amino-2-deoxy Sugar Derivatives by a Free-Radical Procedure." @default.
- W2949803873 cites W1967134392 @default.
- W2949803873 doi "https://doi.org/10.1002/chin.199850240" @default.
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