2,3-O-(1-methylethylidene)-4,5-O-thiocarbonyl-β-D-fructopyranose sulfamate | 161721-32-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 2,3-O-(1-methylethylidene)-4,5-O-thiocarbonyl-β-D-fructopyranose sulfamate
• 英文别名: [(1R,2S,6S,9R)-4,4-dimethyl-11-sulfanylidene-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methyl sulfamate
• CAS: 161721-32-0
• 化学式: C₁₀H₁₅NO₈S₂
• 分子量: 341.363
• InChiKey: BVEAEQLEXSWOEQ-JQCUSGDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  156
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,3-O-(1-methylethylidene)-4,5-O-thiocarbonyl-β-D-fructopyranose sulfamate 在 碘甲烷 作用下， 以 乙二醇二甲醚 为溶剂， 反应 2.5h， 以23%的产率得到Sulfamic acid (3aS,5aR,8aR,8bS)-2,2-dimethyl-7-oxo-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-ylmethyl ester
  参考文献：
  名称：

  Non-chair six-membered-ring conformations. Preference for a twist-boat (or skew) structure in α-L-sorbopyranose derivatives

  摘要：

  The conformational preferences for 2,3-O-isopropylidene-alpha-L-sorbopyranose derivatives 3-6 were determined by using H-1 NMR data and empirical force field calculations. Proton NMR studies of 3-6 indicate that a twist-boat (or skew) conformation (S-3(0)) prevails over possible chair forms for each compound. Force-field calculations (MM2, MNDO, AM1) on a model 2,3-O-isopropylidene-alpha-L-sorbopyranose system (18) indicate that the S-3(0) conform ation is among the low-energy structures. X-Ray crystallographic analysis of alpha-L-sorbopyranose sulfamate 3, a compound with potent anticonvulsant activity, demonstrates that the S-3(0) skew conformation is manifested in the solid state, as well.

  DOI：

  10.1016/s0957-4166(00)80393-6
• 作为产物：
  描述：

  2,3-O-(1-甲基亚乙基)-beta-D-吡喃果糖1-氨基磺酸酯 、 N,N'-硫羰基二咪唑 在 盐酸 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 以15.0 g (40%)的产率得到2,3-O-(1-methylethylidene)-4,5-O-thiocarbonyl-β-D-fructopyranose sulfamate
  参考文献：
  名称：

  Anticonvulsant sorbopyranose sulfamates

  摘要：

  具有以下式子（I）的磺酰胺衍生物：##STR1## 其中R.sub.1，R.sub.2，R.sub.3，R.sub.4，R.sub.5和R.sub.6如所定义，已被发现具有抗惊厥活性，因此在治疗癫痫等疾病方面非常有用。此外，本发明还包括含有式（I）化合物的制药组合物，以及使用它们的方法和新的中间体。

  公开号：

  US05384327A1

文献信息

• Anticonvulsant sorbopyranose sulfamates
  申请人：McNeilab, Inc.

  公开号：US05384327A1

  公开（公告）日：1995-01-24

  Sulfamate derivatives having the following formula (I): ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are as herein defined, have been found to exhibit anticonvulsant activity and are thus useful in the treatment of conditions such as epilepsy. Further, the present invention encompasses pharmaceutical compositions containing a compound of formula (I) as well as methods for their use and novel intermediates are disclosed.

  具有以下式子（I）的磺酰胺衍生物：##STR1## 其中R.sub.1，R.sub.2，R.sub.3，R.sub.4，R.sub.5和R.sub.6如所定义，已被发现具有抗惊厥活性，因此在治疗癫痫等疾病方面非常有用。此外，本发明还包括含有式（I）化合物的制药组合物，以及使用它们的方法和新的中间体。
• ANTICONVULSANT SORBOPYRANOSE SULFAMATES
  申请人：MCNEILAB, INC.

  公开号：EP0675893B1

  公开（公告）日：1999-03-03
• 5-halo-5-deoxy sorbopyranose compounds
  申请人：MCNEILAB, INC.

  公开号：EP0869131B1

  公开（公告）日：2002-03-20
• US5384327A
  申请人：——

  公开号：US5384327A

  公开（公告）日：1995-01-24
• Non-chair six-membered-ring conformations. Preference for a twist-boat (or skew) structure in α-L-sorbopyranose derivatives
  作者：Michael J. Costanzo、Harold R. Almond、A.Diane Gauthier、Bruce E. Maryanoff

  DOI：10.1016/s0957-4166(00)80393-6

  日期：1994.12

  The conformational preferences for 2,3-O-isopropylidene-alpha-L-sorbopyranose derivatives 3-6 were determined by using H-1 NMR data and empirical force field calculations. Proton NMR studies of 3-6 indicate that a twist-boat (or skew) conformation (S-3(0)) prevails over possible chair forms for each compound. Force-field calculations (MM2, MNDO, AM1) on a model 2,3-O-isopropylidene-alpha-L-sorbopyranose system (18) indicate that the S-3(0) conform ation is among the low-energy structures. X-Ray crystallographic analysis of alpha-L-sorbopyranose sulfamate 3, a compound with potent anticonvulsant activity, demonstrates that the S-3(0) skew conformation is manifested in the solid state, as well.