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| - A Diastereoselective and General Route to5-Amino-5-deoxysugars: Influence of C-3 Substitution on theAddition of Amines to C-5 of Vinyl Sulfone-ModifiedHex-5-enofuranosyl Carbohydrates
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| - In the synthesis of vinyl sulfone-modified hex-5-enofuranosides, the E/Z ratios of the products areinfluenced by the stereoelectronic property of a group present at the C-3 position. This observationhas been utilized to influence the diastereoselectivity of addition of amines to C-5 of vinyl sulfone-modified hex-5-enofuranosides, which are efficient Michael acceptors. The stereoelectronic effectof OMe attached to the β-face of C-3 (gluco derivative) is sufficient to impose diastereoselectivityoverwhelmingly in favor of l-ido-aminosugars when the Michael acceptor is reacted with bothprimary and secondary amines. 3-O-Benzylated gluco derivative is also effective in producing l-ido-aminosugars but only in reactions with primary amines. The selectivity is lost when an alloderivative with OBn at the α-face of C-3 is used. Selected products were desulfonated to establishthis new approach as a general and versatile strategy for accessing 5-amino-5-deoxysugars.
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