(2R,3R,4R,4aR,4bR,5R,6S,9aR)-3,4-diacetoxy-2-(acetoxymethyl)-5,6-(O-isopropylidene)octahydro-2H-pyrano<3,2-d>pyrrolo<1,2-b>isoxazole | 231277-32-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,4aR,4bR,5R,6S,9aR)-3,4-diacetoxy-2-(acetoxymethyl)-5,6-(O-isopropylidene)octahydro-2H-pyrano<3,2-d>pyrrolo<1,2-b>isoxazole
• 英文别名: [(1R,2R,3R,4S,5R,7R,11S,15R)-3,4-diacetyloxy-13,13-dimethyl-6,8,12,14-tetraoxa-9-azatetracyclo[7.6.0.02,7.011,15]pentadecan-5-yl]methyl acetate
• CAS: 231277-32-0
• 化学式: C₁₉H₂₇NO₁₀
• 分子量: 429.424
• InChiKey: DQVPMPZVRPZVQT-VPHXLKCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,4aR,4bR,5R,6S,9aR)-3,4-diacetoxy-2-(acetoxymethyl)-5,6-(O-isopropylidene)octahydro-2H-pyrano<3,2-d>pyrrolo<1,2-b>isoxazole 在 palladium on activated charcoal 氢气 、 sodium 作用下， 以 甲醇 、 水 为溶剂， 反应 65.0h， 生成 (2'R,3'R,4'S)-2-deoxy-2-<2-(3,4-dihydroxy)pyrrolidinyl>-β-D-glucose
  参考文献：
  名称：

  Complete Stereoselective Synthesis of Quasi-Enantiomeric Pseudo Imino-C-disaccharides: Parallel Kinetic Resolution of a Racemiccis-DihydroxypyrrolineN-Oxide by 1,2-Glycals

  摘要：

  Cycloadditions of hydroxylated enantiopure pyrroline N-oxides to 1,2-glycals display high double-asymmetric induction. The selectivity is controlled by the stereochemistry at C-3 of the glycal. A parallel kinetic resolution experiment with a racemic cis-dihydroxypyrroline N-oxide allowed the synthesis of two different pseudo imino-C-disaccharides precursors in a completely enantiopure form, totally avoiding the formation of minor cycloadducts.

  DOI：

  10.1002/(sici)1099-0690(199906)1999:6<1319::aid-ejoc1319>3.0.co;2-l
• 作为产物：
  描述：

  (2S,3R)-3,4-cis-isopropylidenedioxypyrroline N-oxid 、 乙酰化葡萄烯糖 以 甲苯 为溶剂， 反应 24.0h， 以10%的产率得到(2R,3R,4R,4aR,4bR,5S,6R,9aR)-3,4-diacetoxy-2-(acetoxymethyl)-5,6-(O-isopropylidene)octahydro-2H-pyrano<3,2-d>pyrrolo<1,2-b>isoxazole
  参考文献：
  名称：

  Complete Stereoselective Synthesis of Quasi-Enantiomeric Pseudo Imino-C-disaccharides: Parallel Kinetic Resolution of a Racemiccis-DihydroxypyrrolineN-Oxide by 1,2-Glycals

  摘要：

  Cycloadditions of hydroxylated enantiopure pyrroline N-oxides to 1,2-glycals display high double-asymmetric induction. The selectivity is controlled by the stereochemistry at C-3 of the glycal. A parallel kinetic resolution experiment with a racemic cis-dihydroxypyrroline N-oxide allowed the synthesis of two different pseudo imino-C-disaccharides precursors in a completely enantiopure form, totally avoiding the formation of minor cycloadducts.

  DOI：

  10.1002/(sici)1099-0690(199906)1999:6<1319::aid-ejoc1319>3.0.co;2-l