@article { ISI:000260290900014,
	title = {Diastereoselective addition of planar N-heterocycles to vinyl sulfone-modified carbohydrates: a new route to isonucleosides},
	journal = {Tetrahedron},
	volume = {64},
	number = {45},
	year = {2008},
	month = {NOV},
	pages = {10406-10416},
	publisher = {PERGAMON-ELSEVIER SCIENCE LTD},
	type = {Article},
	address = {THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND},
	abstract = {<p>Michael-type addition reactions of planar N-heterocycles at the C-2 positions of vinyl sulfone-modified carbohydrates provide an efficient and general route for the carbon-N-heterocycle bond formation. Therefore, the addition pattern of planar heterocycles, such as imidazole, triazole, thymine, and adenine to 3-C-phenyisulfonyl-hex-2-enopyranosides (1 alpha/1 beta) and 3-C-p-toluenesulfonyl-pent-2-enofuranosides (2 alpha/2 beta) was studied for developing a general methodology for the synthesis of new classes of isonucleosides possessing a carbon-N-heterocycle linkage at C-2 positions of furanosyl and pyranosyl sugars. To a great extent, the anomeric configurations of the starting vinyl sulfones play crucial roles in deciding the diastereoselectivity of addition of heterocycles. However, the trityl protected 3-C-p-toluenesulfonyl-hex-2-enopyranosides (33 alpha/33 beta) were judged to be More practical starting materials for desulfortylation and deprotection for the synthesis of a new class of thymine and adenine deoxyisonucleosides. (C) 2008 Elsevier Ltd. All rights reserved.</p>},
	issn = {0040-4020},
	doi = {10.1016/j.tet.2008.08.050},
	author = {Sanki, Aditya K. and Bhattacharya, Rahul and Atta, Ananta Kumar and Suresh, Cheravakkattu G. and Pathak, Tanmaya}
}
