N-[(diphenylamino)carbonyl]-2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[(diphenylamino)carbonyl]-2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate
• 英文别名: [(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methyl N-(diphenylcarbamoyl)sulfamate
• 化学式: C₂₅H₃₀N₂O₉S
• 分子量: 534.587
• InChiKey: CRYKQWOUZPNKGE-HSGJQSDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-[(diphenylamino)carbonyl]-2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate 在 水 、 sodium acetate 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 1.5h， 以67%的产率得到托吡酯
  参考文献：
  名称：

  Process for the preparation of topiramate

  摘要：

  本发明涉及一种制备托吡酯的方法，以及在该过程中的中间体和制备这些中间体的方法。

  公开号：

  US20060040874A1
• 作为产物：
  描述：

  Ph2NC(O)NHSO2Cl 、 果糖二丙酮 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-[(diphenylamino)carbonyl]-2,3:4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose sulfamate
  参考文献：
  名称：

  Process for the preparation of topiramate

  摘要：

  本发明涉及一种制备托吡酯的方法，以及该方法中的中间体和制备这些中间体的方法。

  公开号：

  EP1627881A1

文献信息

• Process for the preparation of topiramate
  申请人：Arvai Geza

  公开号：US20060040874A1

  公开（公告）日：2006-02-23

  The present invention relates to a process for the preparation of topiramate, intermediates in this process and a process for the preparation of these intermediates.

  本发明涉及一种制备托吡酯的方法，以及在该过程中的中间体和制备这些中间体的方法。
• Dynamic stereochemistry of Topiramate (anticonvulsant drug) in solution: theoretical approaches and experimental validation
  作者：Mina Ghiasi、Afsaneh Arefi Oskouie、Hamdollah Saeidian

  DOI：10.1016/j.carres.2011.11.010

  日期：2012.2

  Topiramate, an antiepileptic drug, was synthesized with an improved protocol and identified by H-1 NMR, C-13 NMR, H-1-H-1 COSY, HMQC and HMBC spectrum. In parallel, density functional theory (DFT) using B3LYP functional and split-valance 6-311++G** basis set has been used to optimize the structures and conformers of Topiramate. Also experimental and theoretical methods have been used to correlate the dependencies of (1)J and (2)J involving H-1 and C-13 on the C1-C2 (omega) and C1-01 (theta) torsion angles in the glycosidic part of Topiramate. New Karplus equations are proposed to assist in the structural interpretation of these couplings. Importantly, due to the sensitivity of some couplings, most notably (2)J(H1R,H1S), (2)J(C2,H1R) and (2)J(C2,H1S) values depend on both C-C (omega) and C-O (theta) torsion angles. Analyses of experimental coupling constants for protons on the pyranose ring of Topiramate indicate a twist boat structure for Topiramate in solution. In all calculations solvent effects were considered using a polarized continuum model (PCM). (C) 2011 Elsevier Ltd. All rights reserved.