5-O-Benzyl-2,3-didesoxy-2-dimethylamino-3-fluoro-β-D-arabinofuranoside de methyle | 143604-55-1

• 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: 5-O-Benzyl-2,3-didesoxy-2-dimethylamino-3-fluoro-β-D-arabinofuranoside de methyle
• 英文别名: (2R,3R,4S,5R)-4-fluoro-2-methoxy-N,N-dimethyl-5-(phenylmethoxymethyl)oxolan-3-amine
• CAS: 143604-55-1
• 化学式: C₁₅H₂₂FNO₃
• 分子量: 283.343
• InChiKey: IPSZZVGJHHNNLX-APIJFGDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-O-Benzyl-2,3-didesoxy-2-dimethylamino-3-fluoro-β-D-arabinofuranoside de methyle 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 盐酸 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 75.0 ℃ 、100.0 kPa 条件下， 反应 33.5h， 生成 mesylate de 2,5-dimethylepiminio-3-fluoro-2,3,5-tridesoxy-β-D-arabinofuranoside 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：

  2,3-Anhydro-5-O-benzyl-β-D-ribofuranoside de methyle 在 triethylamine tris(hydrogen fluoride) 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 102.5h， 生成 5-O-Benzyl-2,3-didesoxy-2-dimethylamino-3-fluoro-β-D-arabinofuranoside de methyle
  参考文献：
  名称：

  Synthese et equilibre thermodynamique des huit 5-O-benzyl-2- (ou 3)- dimethylamino-3 (ou 2)-O-mesyl-α (ou β)-D- (ou ) - furanosides de methyle

  摘要：

  Regioselectivity of the opening of 2,3-anhydrofuranosides 1 (alpha and beta) and 2 (alpha and beta) by dimethylamine (and by ammonia for 1) has been determined. Thermic stability of the eight corresponding vic-dimethylaminomesylates 11-14 (alpha and beta) in CD3CN and C6D6 has been studied by H-1 NMR : in each case steric hindrance seems to be the determinant factor of the four thermodynamic equilibria 11 reversible 12 (alpha and beta) and 13 reversible 14 (alpha and beta); aziridinium ions are assumed to be formed as intermediates and one of them has been effectively observed.

  DOI：

  10.1016/s0040-4020(01)90122-x

文献信息

• Synthese et equilibre thermodynamique des huit 5-O-benzyl-2- (ou 3)- dimethylamino-3 (ou 2)-O-mesyl-α (ou β)-D- (ou ) - furanosides de methyle
  作者：Marie-Béatrice Giudicelli、Marie-Agnès Thomé、Dominique Picq、Daniel Anker

  DOI：10.1016/s0040-4020(01)90122-x

  日期：1992.1

  Regioselectivity of the opening of 2,3-anhydrofuranosides 1 (alpha and beta) and 2 (alpha and beta) by dimethylamine (and by ammonia for 1) has been determined. Thermic stability of the eight corresponding vic-dimethylaminomesylates 11-14 (alpha and beta) in CD3CN and C6D6 has been studied by H-1 NMR : in each case steric hindrance seems to be the determinant factor of the four thermodynamic equilibria 11 reversible 12 (alpha and beta) and 13 reversible 14 (alpha and beta); aziridinium ions are assumed to be formed as intermediates and one of them has been effectively observed.
• 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.