1309358-03-9Relevant articles and documents
An isofagomine analogue with an amidine at the pseudoanomeric position
Lindbaeck, Emil,Lopez, Oscar,Fernandez-Bolanos, Jose G.,Sauer, Stephan P. A.,Bols, Mikael
supporting information; experimental part, p. 2908 - 2911 (2011/08/03)
(3R,4R,5R)-2-Imino-3,4-dihydroxy-5-hydroxymethylpiperidine hydrocloride or isofagomidine was synthesized from d-arabinose in 12 steps and an overall yield of 9.9%. The synthesis proceeded by introduction of an aminomethyl group in the 4-position of d-arabinose and conversion of C-1 into a nitrile. The key step in the synthesis was a copper-catalyzed cyclization of aminonitrile to amidine. Isofagomidine was a potent α-mannosidase inhibitor (Ki = 0.75 μM).