Methanesulfonic acid (1R,2R,3S,4S,5R)-2,4-bis-methanesulfonyloxy-8-oxa-6-aza-bicyclo[3.2.1]oct-3-yl ester | 225663-14-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: Methanesulfonic acid (1R,2R,3S,4S,5R)-2,4-bis-methanesulfonyloxy-8-oxa-6-aza-bicyclo[3.2.1]oct-3-yl ester
• 英文别名: [(1R,2R,3S,4S,5R)-3,4-bis(methylsulfonyloxy)-8-oxa-6-azabicyclo[3.2.1]octan-2-yl] methanesulfonate
• CAS: 225663-14-9
• 化学式: C₉H₁₇NO₁₀S₃
• 分子量: 395.433
• InChiKey: MCBCXROYZPWCSJ-XGQMLPDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  177
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (1R,2R,3S,4S,5R)-2,4-bis-methanesulfonyloxy-8-oxa-6-aza-bicyclo[3.2.1]oct-3-yl ester 在 氢气 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 2.0h， 以85%的产率得到Methanesulfonic acid (2R,3S,4S,5R,6R)-2,6-dihydroxy-3,5-bis-methanesulfonyloxy-azepan-4-yl ester
  参考文献：
  名称：

  Efficient synthesis of seven-membered iminocyclitols from glycosylenamines

  摘要：

  Seven membered iminocyclitols are synthesized in four steps from easily available glycosylenamines (D-gluco, D-galacto, and D-manno configurations) through 1,6-aza-anhydrosugar derivatives. These intermediates are transformed into 2-hydroxy- and 2-unsubstituted azepanes depending on the reactants used for the cleavage of the C1-O bond. The overall yields are high. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00649-8
• 作为产物：
  描述：

  N-(2,2-diethoxycarbonylvinyl)-2,3,4,6-tetra-O-mesyl-β-D-mannopyranosylamine 在 sodium methylate 、 氯 作用下， 以 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 生成 Methanesulfonic acid (1R,2R,3S,4S,5R)-2,4-bis-methanesulfonyloxy-8-oxa-6-aza-bicyclo[3.2.1]oct-3-yl ester
  参考文献：
  名称：

  Efficient synthesis of seven-membered iminocyclitols from glycosylenamines

  摘要：

  Seven membered iminocyclitols are synthesized in four steps from easily available glycosylenamines (D-gluco, D-galacto, and D-manno configurations) through 1,6-aza-anhydrosugar derivatives. These intermediates are transformed into 2-hydroxy- and 2-unsubstituted azepanes depending on the reactants used for the cleavage of the C1-O bond. The overall yields are high. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00649-8