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  • Title: Stereodivergent de novo synthesis of branched amino sugars by lewis Acid promoted rearrangement of 1,2-oxazines.
    Author: Pfrengle F, Lentz D, Reissig HU.
    Journal: Angew Chem Int Ed Engl; 2009; 48(17):3165-9. PubMed ID: 19322866.
    Abstract:
    Well concealed: 1,2-oxazines such as 1 rearrange under Lewis acidic conditions to bicyclic products of type 2, which can be incorporated into oligosaccharides as protected amino sugar equivalents. Subsequent reductive steps provide unusual oligosaccharides 3 having C2-branched 4-amino sugar units. Most of the reactions proceed with excellent stereocontrol and allow the synthesis of a collection of stereoisomers.
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