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Updated: May 26, 2026

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
Published on: September 9, 2016
Guanidinium 2-(myristoylsulfanyl)ethane-sulfonate
Elizabeth S Monillas1, Wesley H Monillas, Eric R Sirianni
1Department of Chemistry and Biochemistry, University of Delaware, Newark, DE 19716, USA.
Abstract:
In the title compound, CH(6)N(3) (+)·C(16)H(31)O(4)S(2) (-) [systematic name: guanidinium 2-(tetra-deca-noylsulfan-yl)ethane-sulfon-ate], each 2-(myristoyl-thio)-ethane-sulfonate ion displays hydrogen bonding to three guanidinium counter-ions, which themselves display hydrogen bonding to two symmetry-related 2-(myristoylthio)ethanesulfonate ions. Thus each cation forms six N-H⋯O bonds to neighboring anions, thereby self-assembling an extended ladder-type network. The average hydrogen-bond donor-acceptor distance is 2.931 (5) Å. The alkyl chains form the rungs of a ladder with hydrogen-bonding inter-actions forming the side rails.

