Betulin 3,28-di-O-tosyl-ate

Acta Crystallogr Sect E Struct Rep Online. 2014 Jul 23;70(Pt 8):o879-80. doi: 10.1107/S1600536814016602. eCollection 2014 Aug 1.

Abstract

The title compound, C44H62O6S2 {systematic name: (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-penta-methyl-1-(prop-1-en-2-yl)-3a-[(tos-yloxy)meth-yl]icosa-hydro-1H-cyclo-penta-[a]chrysen-9-yl 4-methyl-benzene-sulfonate}, was obtained by tosyl-ation of naturally occurring betulin. All the cyclo-hexane rings adopt chair conformations and the cyclo-pentane ring adopts a twisted envelope conformation, with the C atom bearing the tosyl-methyl substituent forming the flap. In the crystal, mol-ecules form a three-dimensional network through multiple weak C-H⋯O hydrogen bonds.

Keywords: betulin 3,28-di-O-tosyl­ate; crystal structure; hydrogen bonding; natural product.