5-O-Benzyl-2-desoxy-2-dimethylamino-3-O-methanesulfonyl-α-D-arabinofuranoside de methyle | 143604-44-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-Benzyl-2-desoxy-2-dimethylamino-3-O-methanesulfonyl-α-D-arabinofuranoside de methyle
• 英文别名: [(2R,3S,4S,5S)-4-(dimethylamino)-5-methoxy-2-(phenylmethoxymethyl)oxolan-3-yl] methanesulfonate
• CAS: 143604-44-8
• 化学式: C₁₆H₂₅NO₆S
• 分子量: 359.444
• InChiKey: ARVIKQHNQQZFRX-QXSJWSMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-O-Benzyl-2-desoxy-2-dimethylamino-3-O-methanesulfonyl-α-D-arabinofuranoside de methyle 在 氢氟酸 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以80%的产率得到5-O-benzyl-2,3-didesoxy-2-dimethylamino-3-fluoro-α-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-α-D-ribofuranoside de methyle 在 ammonium hydroxide 、 甲酸 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 45.75h， 生成 5-O-Benzyl-2-desoxy-2-dimethylamino-3-O-methanesulfonyl-α-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.