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Paper | Regular issue | Vol 29, No. 6, 1989, pp.1171-1177
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4932
A Reconfirmation of the Reaction of Glucosyl Isothiocyanate with 2-Chloroethylamine

Haruo Ogura,* Kazuyoshi Takeda, and Hiroaki Takayanagi

*School of Pharmaceutical Sciences, Kitasato University, 5-9-1, Shirokane, Minato-ku, Tokyo 108-8641, Japan


The reaction of tetra-O-acetylglucosyl isothiocyanate (1) with 2-chloroethylamine under basic conditions in aprotic solvent afforded 2-(2’,3’,4’,6’-tetra-O-acetyl-β-D- glucopyranosylamino)-2-thiazoline (2). On the other hand, in Pyridine solution this reaction proceeded to form N, N’-bis(2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranosyl)-N-(2-thiazolin-2-yl)thiourea (3). Alkaline hydrolysis of 2 afforded 2-(β-D-glucopyranosylamino)-2-thiazoline (4) as colorless plates, which was confirmed by means of X-ray analysis.