A diastereoselective and general route to 5-amino-5-deoxysugars: influence of C-3 substitution on the addition of amines to C-5 of vinyl sulfone-modified hex-5-enofuranosyl carbohydrates

Das, Indrajit ; Pathak, Tanmaya ; Suresh, Cheravakkattu G. (2005) A diastereoselective and general route to 5-amino-5-deoxysugars: influence of C-3 substitution on the addition of amines to C-5 of vinyl sulfone-modified hex-5-enofuranosyl carbohydrates The Journal of Organic Chemistry, 70 (20). pp. 8047-8054. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo051143c

Related URL: http://dx.doi.org/10.1021/jo051143c

Abstract

In the synthesis of vinyl sulfone-modified hex-5-enofuranosides, the E/Z ratios of the products are influenced by the stereoelectronic property of a group present at the C-3 position. This observation has 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 effect of OMe attached to the β-face of C-3 (gluco derivative) is sufficient to impose diastereoselectivity overwhelmingly in favor of ʟ-ido-aminosugars when the Michael acceptor is reacted with both primary 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 allo derivative with OBn at the α-face of C-3 is used. Selected products were desulfonated to establish this new approach as a general and versatile strategy for accessing 5-amino-5-deoxysugars.

Item Type:Article
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