2,3-didesoxy-3-dimethylamino-2-fluoro-5-O-methanesulfonyl-β-D-xylofuranoside de methyle | 143996-18-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 2,3-didesoxy-3-dimethylamino-2-fluoro-5-O-methanesulfonyl-β-D-xylofuranoside de methyle
• 英文别名: [(2S,3S,4R,5R)-3-(dimethylamino)-4-fluoro-5-methoxyoxolan-2-yl]methyl methanesulfonate
• CAS: 143996-18-3
• 化学式: C₉H₁₈FNO₅S
• 分子量: 271.31
• InChiKey: MGZURILVRWSIHV-LURQLKTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  73.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3-didesoxy-3-dimethylamino-2-fluoro-5-O-methanesulfonyl-β-D-xylofuranoside de methyle 在 氢氟酸 、 三乙胺 作用下， 反应 20.0h， 生成 2,5-difluoro-3-dimethylamino-2,3,5-tridesoxy-β-D-xylofuranoside de methyle
  参考文献：
  名称：

  Formation competitive d'ions azetidinium, pyrrolidinium et aziridinium lors de la fluoration de quelques dimethylaminopentofuranosides di-O-mesyles

  摘要：

  5-O-mesylated furanosides such as 3-dimethylamino-D-xylo (2-beta and 10-beta) or 2-dimethylamino-D-arabino (1-alpha, 7-alpha and 7-beta) readily afford a new class of bicyclic compounds with an azetidinium or a pyrrolidinium ring ; whenever competitive aziridinium ion can be obtained (in the case of 3,5 or 2,5 dimesylates), formation of four or five-membered ring is mainly observed : these ions seem quite unreactive towards fluorinating agents.

  DOI：

  10.1016/s0040-4020(01)89851-3
• 作为产物：
  描述：

  5-O-Benzyl-2,3-didesoxy-3-dimethylamino-2-fluoro-β-D-xylofuranoside de methyle 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 盐酸 、 乙醇 、 二氯甲烷 为溶剂， 反应 25.5h， 生成 2,3-didesoxy-3-dimethylamino-2-fluoro-5-O-methanesulfonyl-β-D-xylofuranoside de methyle
  参考文献：
  名称：

  Formation competitive d'ions azetidinium, pyrrolidinium et aziridinium lors de la fluoration de quelques dimethylaminopentofuranosides di-O-mesyles

  摘要：

  5-O-mesylated furanosides such as 3-dimethylamino-D-xylo (2-beta and 10-beta) or 2-dimethylamino-D-arabino (1-alpha, 7-alpha and 7-beta) readily afford a new class of bicyclic compounds with an azetidinium or a pyrrolidinium ring ; whenever competitive aziridinium ion can be obtained (in the case of 3,5 or 2,5 dimesylates), formation of four or five-membered ring is mainly observed : these ions seem quite unreactive towards fluorinating agents.

  DOI：

  10.1016/s0040-4020(01)89851-3

文献信息

• Formation competitive d'ions azetidinium, pyrrolidinium et aziridinium lors de la fluoration de quelques dimethylaminopentofuranosides di-O-mesyles
  作者：Marie-Béatrice Giudicelli、Picq Dominique、Anker Daniel

  DOI：10.1016/s0040-4020(01)89851-3

  日期：1992.1

  5-O-mesylated furanosides such as 3-dimethylamino-D-xylo (2-beta and 10-beta) or 2-dimethylamino-D-arabino (1-alpha, 7-alpha and 7-beta) readily afford a new class of bicyclic compounds with an azetidinium or a pyrrolidinium ring ; whenever competitive aziridinium ion can be obtained (in the case of 3,5 or 2,5 dimesylates), formation of four or five-membered ring is mainly observed : these ions seem quite unreactive towards fluorinating agents.