5-O-Benzyl-3-desoxy-3-dimethylamino-β-D-arabinofuranoside de methyle | 143617-35-0

• 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-3-desoxy-3-dimethylamino-β-D-arabinofuranoside de methyle
• 英文别名: (2R,3S,4S,5S)-4-(dimethylamino)-2-methoxy-5-(phenylmethoxymethyl)oxolan-3-ol
• CAS: 143617-35-0
• 化学式: C₁₅H₂₃NO₄
• 分子量: 281.352
• InChiKey: UXBGQMHDYKZMQS-APIJFGDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 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：
  51.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-O-Benzyl-3-desoxy-3-dimethylamino-β-D-arabinofuranoside de methyle 在 氘代苯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 Methanesulfonate(1S,2S,4R,5R)-2-benzyloxymethyl-4-methoxy-6,6-dimethyl-3-oxa-6-azonia-bicyclo[3.1.0]hexane;
  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
• 作为产物：
  描述：

  methyl 5-O-benzyl-2,3-anhydro-β-D-lyxofuranoside 、 二甲胺 以 水 为溶剂， 反应 5.5h， 生成 5-O-Benzyl-2-desoxy-2-dimethylamino-β-D-xylofuranoside de methyle 、 5-O-Benzyl-3-desoxy-3-dimethylamino-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