Crystal structures of sulfonamide protected bicyclic guanidines: ( S )-8-{[( tert -butyl-dimethyl-sil-yl)-oxy]meth-yl}-1-[(2,2,4,6,7-penta-methyl-2,3-di-hydro-benzo-furan-5-yl)sulfon-yl]-1,3,4,6,7,8-hexa-hydro-2 H -pyrimido[1,2- a ]pyrimidin-1-ium tri-fluoro-methane-sulfonate and ( S )-8-(iodo-meth-yl)-1-tosyl-1,3,4,6,7,8-hexa-hydro-2 H -pyrimido[1,2- a ]pyrimidin-1-ium iodide

• Published in: Acta crystallographica. Section E, Crystallographic communications Vol. 80; no. Pt 3; p. 305
• Main Authors: Alaboosh, Jamal M H, Hill, Steven P, Kariuki, Benson M, Redman, James E
• Format: Journal Article
• Language: English
• Published: England 01.03.2024
• Subjects: Pbf; crystal structure; tos­yl; bicyclic guanidine
• ISSN: 2056-9890; 2056-9890

Two compounds, ( )-8-{[( -butyl-dimethyl-sil-yl)-oxy]meth-yl}-1-[(2,2,4,6,7-penta-methyl-2,3-di-hydro-benzo-furan-5-yl)sulfon-yl]-1,3,4,6,7,8-hexa-hydro-2 -pyrimido[1,2- ]pyrimidin-1-ium tri-fluoro-methane-sulfonate, C H N O SSi ·CF O S , ( ) and ( )-8-(iodo-meth-yl)-1-tosyl-1,3,4,6,7,8-hexa-hydro-2 -pyrimido[1,2- ]pyrimidin-1-ium iodide, C H IN O S ·I , ( ), have been synthesized and characterized. They are bicyclic guanidinium salts and were synthesized from -( -but-oxy-carbon-yl)-l-me-thio-nine (Boc-l-Met-OH). The guanidine is protected by a 2,2,4,6,7-penta-methyl-dihydro-benzo-furan-5-sulfonyl (Pbf, ) or a tosyl ( ) group. In the crystals of both compounds, the guanidinium group is almost planar and the N-H forms an intra-molecular hydrogen bond in a six-membered ring to the oxygen atom of the sulfonamide protecting group.