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- W2950563775 abstract "Abstract Iodoacetoxylation of 3,6-di- O -acetyl-4- O -(2,3,4,6-tetra- O -acetyl-β- d -galactopyranosyl)-1,5-anhydro-2-deoxy- d - arabino -hex-1-enitol (hexa- O -acetyllactal) and the corresponding hexa- O -benzoyl derivative, gave the α-1,2- trans 1- O -acetyl-2-deoxy-2-iodo adducts with high stereoselectivity and good yields. These were treated with an excess of trimethylsilyl azide in the presence of trimethylsilyl trifluoromethanesulfonate affording the corresponding α-1,2- trans 2-deoxy-2-iodoglycosyl azides. In the presence of an alcohol, a Staudinger reaction at the anomeric azide ledin situ to an iminophosphorane which rearranged with elimination of iodine at C-2. The aziridine intermediate thus obtained reacted with a suitable alcohol to afford the corresponding lactosamine β-glycosides. The reaction occurred with double inversion of configuration at C-1 and C-2. Deprotection of the amine functionality and further transformation into the acetamido derivatives could be achieved without isolation of the intermediates. © 1997 Elsevier Science Ltd." @default.
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- W2950563775 date "2010-08-03" @default.
- W2950563775 modified "2023-09-24" @default.
- W2950563775 title "ChemInform Abstract: A Convenient Access to β-Glycosides of N-Acetyllactosamine." @default.
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- W2950563775 doi "https://doi.org/10.1002/chin.199722224" @default.
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