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.
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 beta-face of C-3 (gluco derivative) is sufficient to impose diastereoselectivity overwhelmingly in favor of l-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 alpha-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.
Das
Indrajit
I
Department of Chemistry, Indian Institute of Technology, Kharagpur 721 302, India.
Pathak
Tanmaya
T
Suresh
Cheravakkattu G
CG
D000588:Amines; D000606:Amino Sugars / Q000138:chemical synthesis*; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000138:chemical synthesis*; D003837:Deoxy Sugars / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008958:Models, Molecular; D013450:Sulfones; D014753:Vinyl Compounds
D000588:Amines; D000606:Amino Sugars; D002241:Carbohydrates; D003837:Deoxy Sugars; D007202:Indicators and Reagents; D013450:Sulfones; D014753:Vinyl Compounds