(2R,3R,4R,4aR,4bR,5R,6S,9aR)-3,4-dihydroxy-2-(hydroxymethyl)-5,6-(O-isopropylidene)octahydro-2H-pyrano<3,2-d>pyrrolo<1,2-b>isoxazole | 231277-36-4

• 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-dihydroxy-2-(hydroxymethyl)-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)-5-(hydroxymethyl)-13,13-dimethyl-6,8,12,14-tetraoxa-9-azatetracyclo[7.6.0.02,7.011,15]pentadecane-3,4-diol
• CAS: 231277-36-4
• 化学式: C₁₃H₂₁NO₇
• 分子量: 303.312
• InChiKey: UNQXZHILWJNVHS-BLXNTMOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,4aR,4bR,5R,6S,9aR)-3,4-dihydroxy-2-(hydroxymethyl)-5,6-(O-isopropylidene)octahydro-2H-pyrano<3,2-d>pyrrolo<1,2-b>isoxazole 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 53.0h， 生成 (2'R,3'R,4'S)-2-deoxy-2-<2-(3,4-dihydroxy)pyrrolidinyl>-α-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：

  乙酰化葡萄烯糖 在 sodium 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 36.0h， 生成 (2R,3R,4R,4aR,4bR,5R,6S,9aR)-3,4-dihydroxy-2-(hydroxymethyl)-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

文献信息

• Complete Stereoselective Synthesis of Quasi-Enantiomeric Pseudo Imino-C-disaccharides: Parallel Kinetic Resolution of a Racemiccis-DihydroxypyrrolineN-Oxide by 1,2-Glycals
  作者：Francesca Cardona、Silvia Valenza、Andrea Goti、Alberto Brandi

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

  日期：1999.6

  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.