Gregory Love - Concept and Synthetic Approach for a Kilorgram Scale Synthesis of Octa-D-arginine Amide Nonahydrochloride Salt

Document created by Gregory Love on Aug 22, 2014Last modified by Gregory Love on Feb 2, 2016
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  Publication Details (including relevant citation   information):

  J.C. Califano, A. Uriba, J.L. Chang, C.L. Becker, J.J. Napier, V.   Kishore, D. Zhou, G. Love, K. Gernhardt, and J.C. Tolle,   Tetrahedron, 61, 8821 (2005)


  Oligomers of arginine, such as octa-D-arginine amide, are   excellent transporters for active drugs through cell membranes   and tissue. The synthesis of octa-D-arginine amide, as the   nonahydrochloride salt, was approached via a solution phase   synthetic route involving guanidinylation step. The multi-step   synthesis was carried out at pilot scale, resulting in the   preparation of 700 g of the target molecule. No chomatographic   purification was needed at any step of the process.

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