The Journal of Organic Chemistry

Synthetic Nucleosides. LVIII. 1, 2 Studies on the Synthesis of cis-2, 3-Diamino Sugars. I. The Nitroguanidine Neighboring Group

BR Baker, T Neilson

Index: Baker,B.R.; Neilson,T. Journal of Organic Chemistry, 1964 , vol. 29, p. 1047 - 1050

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Citation Number: 10

Abstract

September. 96, 1963 l-(ZMesyloxyethyl)-3-nitroguanidine (XIV) rapidly cyclized in pyridine at 40'to the imidazoline (XV), a precursor to the ethylenediamine system formed by a neighboring group reaction. In contrast, the sugar pyranoside, methyl 4, 6-0-benzylidene-3- deoxy-2-0-mesyl-3-(3-nitroguanidino)-c~,~-altropyranoside (XXII), failed to cyclize even in boiling pyridine. Anionic cyclization of XXII with a strong base led to the ...