1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose 5-(N-methyloxime) | 53372-93-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose 5-(N-methyloxime)
• 英文别名: C-(1,2-O-Isopropylidene-α-D-xylo-tetrofuranos-4-yl)-N-methylnitrone；1-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-N-methylmethanimine oxide
• CAS: 53372-93-3；146864-61-1
• 化学式: C₉H₁₅NO₅
• 分子量: 217.222
• InChiKey: LIHYSLVJYLXNRM-JHZPRZRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose 5-(N-methyloxime) 在 sodium tetrahydroborate 、 C₂H₆O*Na⁽¹⁺⁾ 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 49.0h， 生成 <(4S)-4-diethoxyphosphorylperhydro-1,3-oxazino><6,5-c>(1,2-O-isopropylidene-α-D-xylo-tetrofuranose)
  参考文献：
  名称：

  α-脱氧-α-羟氨基糖膦酸酯和相应的一氧化氮自由基

  摘要：

  摘要用亚磷酸二烷基酯处理糖醛亚硝基酮可得到糖α-脱氧-α-（N-羟基-N-甲基氨基）膦酸酯，通常具有很高的立体选择性。重复将亲核试剂添加到硝酮中，然后氧化所得羟胺，可生成“第一代”硝酮，即1,2-O-异亚丙基-α-d-二甲苯基-戊二醛-1,4-呋喃糖5-（N-甲基肟），转化为“第三代”环状硝酮，[（4 R）-4-二乙氧基磷酰基-5 H，6 H -1,3-恶嗪基] [6,5- c]（1,2- O-异亚丙基- α-d-木糖-四呋喃糖）N-氧化物。所制备的所有新化合物的构象和构象分配均基于短程和长程H，H，H，P和P，C偶联，并提出了有关长程H，P偶联的新经验规则。

  DOI：

  10.1016/0008-6215(85)85211-3
• 作为产物：
  描述：

  N-甲基羟胺 、 1,2-O-异亚丙基-alpha-D-木糖基-戊二醛-1,4-呋喃糖 以96%的产率得到1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose 5-(N-methyloxime)
  参考文献：
  名称：

  Preparation and stereoselectivity of 1,3-dipolar cycloaddition of C-glycosyl nitrones to N-arylmaleimides

  摘要：

  The cycloaddition of 3'-hydroxyglycosyl-N-methylnitrone (1) to N-arylmaleimides gave the syn isoxazolidines 6, whereas 3'-acetoxyglycosyl-N-methylnitrone (2) afforded the anti isoxazolidines 8 and 10. The formation of 6 was rationalized by an exo attack, stereoelectronically preferred through the hydrogen bond between the pentose hydroxyl group and one of the carbonyl groups of N-arylmaleimide. The sterically preferred endo attack avoiding the repulsions between N-arylmaleimide and sugar moiety was proposed for addition of 2. The structure and steric configuration of the products have been assigned on the basis of H-1 and C-13-NMR spectroscopy, mainly by nuclear Overhauser effect difference spectroscopy. AM1 calculations of the nitrones and MM2 calculations of the adducts were performed.

  DOI：

  10.1007/bf00810931

文献信息

• Radicaux libres dérivés de sucres. V. Dérivés d'osamines N-hydroxylées et composés voisins Communication préliminaire
  作者：Jean M. J. Tronchet、Dominique Schwarzenbach、Eva Winter-Mihaly、Charalambos Diamantides、Ubavka Likić、Griselda Galland-Barrera、Chantal Jorand、Kemal Deen Pullie、Joëlle Ojha-Poncet、Joyce Rupp、Gilles Moret、Micjiel Geoffrey

  DOI：10.1002/hlca.19820650512

  日期：1982.7.28

  Free sugar radicals. V. Deoxyhydroxylaminosugar derivatives and related compounds

  游离糖基。五，脱氧羟氨基糖衍生物及相关化合物
• Preparation and stereoselectivity of 1,3-dipolar cycloaddition of C-glycosyl nitrones to N-arylmaleimides
  作者：Usama A. R. Al-Timari、Lubor Fišera、Peter Ertl、Igor Goljer、Nada Prónayová

  DOI：10.1007/bf00810931

  日期：1992.11

  The cycloaddition of 3'-hydroxyglycosyl-N-methylnitrone (1) to N-arylmaleimides gave the syn isoxazolidines 6, whereas 3'-acetoxyglycosyl-N-methylnitrone (2) afforded the anti isoxazolidines 8 and 10. The formation of 6 was rationalized by an exo attack, stereoelectronically preferred through the hydrogen bond between the pentose hydroxyl group and one of the carbonyl groups of N-arylmaleimide. The sterically preferred endo attack avoiding the repulsions between N-arylmaleimide and sugar moiety was proposed for addition of 2. The structure and steric configuration of the products have been assigned on the basis of H-1 and C-13-NMR spectroscopy, mainly by nuclear Overhauser effect difference spectroscopy. AM1 calculations of the nitrones and MM2 calculations of the adducts were performed.
• α-Deoxy-α-hydroxyamino sugar phosphonates and the corresponding nitroxide free-radicals
  作者：Jean M.J. Tronchet、Eva Winter-Mihaly、Joyce Rupp、Francoise Barbalat-Rey、Michel Geoffroy

  DOI：10.1016/0008-6215(85)85211-3

  日期：1985.2

  gave sugar α-deoxy-α-( N -hydroxy- N -methylamino)phosphonates, often highly stereoselectively. Repeated nucleophilic addition to a nitrone followed by oxidation of the resulting hydroxylamine allows the “first generation” nitrone, 1,2- O -isopropylidene-α- d - xylo -pentodialdo-1,4-furanose 5-( N -methyloxime), to be converted into the “third generation” cyclic nitrone, [(4 R )-4-diethoxyphosphoryl-5

  摘要用亚磷酸二烷基酯处理糖醛亚硝基酮可得到糖α-脱氧-α-（N-羟基-N-甲基氨基）膦酸酯，通常具有很高的立体选择性。重复将亲核试剂添加到硝酮中，然后氧化所得羟胺，可生成“第一代”硝酮，即1,2-O-异亚丙基-α-d-二甲苯基-戊二醛-1,4-呋喃糖5-（N-甲基肟），转化为“第三代”环状硝酮，[（4 R）-4-二乙氧基磷酰基-5 H，6 H -1,3-恶嗪基] [6,5- c]（1,2- O-异亚丙基- α-d-木糖-四呋喃糖）N-氧化物。所制备的所有新化合物的构象和构象分配均基于短程和长程H，H，H，P和P，C偶联，并提出了有关长程H，P偶联的新经验规则。