Research Article: [(3aS,5aR,8aR,8bS)-2,2,7,7-Tetra­methyl­tetra­hydro-3aH-bis­[1,3]dioxolo[4,5-b:4′,5′-d]pyran-3a-yl]methyl (R)-N-(1-phenyl­eth­yl)sulfamate

Date Published: May 01, 2012

Publisher: International Union of Crystallography

Author(s): Meng Xie, Si-Si Shen, Bao-Feng Chen, Yu Sha.


In the title compound, C20H29NO8S, the two five-membered rings adopt envelope conformations (with an O atom at the flap in each case), while the six-membered pyran ring displays a twist-boat conformation. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds into a supra­molecular chain running along the a axis.

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For general background to the drug topiramate [systematic name: 2,3:4,5-bis-O-(1-methyl­ethyl­idene)-beta-d-fructopyran­ose sulfamate] and its potential bioactivity, see: Maryanoff (2009 ▶); Maryanoff et al. (2008 ▶). For related structures, see: Maryanoff et al. (1998 ▶); Winum et al. (2006 ▶).