207857-15-6 | 1,3-Di-Boc-2-(trifluoromethylsulfonyl)guanidine

CAS:207857-15-6 | 1,3-Di-Boc-2-(trifluoromethylsulfonyl)guanidine ,Description

1,3-Di-Boc-2-(trifluoromethylsulfonyl)guanidine, commonly referred to as DBTMS, is an organosulfur compound that has been used in a variety of scientific and industrial applications. It is a bifunctional reagent that has been used for a variety of synthetic transformations, including the synthesis of heterocyclic compounds and the formation of carbon-carbon bonds. DBTMS is also used as a catalyst in a variety of industrial processes, such as the production of pharmaceuticals, agrochemicals, and polymers.
 

Scientific Research Applications

• Synthesis of Hydroxylamine-Containing Analogues of GC7:

  • It was demonstrated that 1,3-di-Boc-2-(trifluoromethylsulfonyl)guanidine can specifically amidinate the amino group in the presence of the free aminooxy group. This discovery aids in synthesizing novel GC7 analogues for investigating their interaction with deoxyhypusine synthase (Khomutov et al., 2016).

• Development in Preparation of Guanidines:

  • The paper presented developments in the preparation of guanidines, including bis(Boc) aminoalkylguanidines, using 1,3-di-Boc-2-(trifluoromethylsulfonyl)guanidine. This method yielded stable sulfonate salts without chromatography, offering a streamlined approach to synthesizing guanidine functionalized building blocks (Hickey et al., 2015).

• Use in Peptide Synthesis:

  • The trifluoroacetyl moiety, a new protecting group for guanidine functionality, is easily cleaved under mild basic conditions. This is complementary to Boc, Cbz, and Ddpe protecting groups and can be applied in peptide synthesis in solution and on a solid phase (Bartoli et al., 2003).

• Method for the Synthesis of N,N′-Di-Boc-Protected Guanidines:

  • An efficient synthetic procedure for converting a variety of amines to N,N′-di-Boc-protected guanidines was described. This method uses cyanuric chloride as an activating reagent for di-Boc-thiourea, offering an alternative route for guanylation of amines (Porcheddu et al., 2009).

• Application in Antibacterial Cotton Fabrics:

  • A tert‐butoxycarbonyl (Boc) protected guanidine containing isocyanate group (IGUA-Boc) was developed and bonded onto cotton fabric. This resulted in antibacterial cotton fabrics with negligible cytotoxicity, maintaining their mechanical properties and antibacterial effectiveness even after 50 laundering cycles (Cao et al., 2020).

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