methyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanose oxime | 202212-55-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanose oxime
• 英文别名: N-[[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methylidene]hydroxylamine
• CAS: 202212-55-3
• 化学式: C₉H₁₅NO₅
• 分子量: 217.222
• InChiKey: JRRQBTMWCCHQKU-WCTZXXKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  69.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二乙烯基砜 、 methyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanose oxime 以 甲苯 为溶剂， 反应 72.0h， 以52%的产率得到1(R),5(S),4'(R),8(S)-8-<4'-(methyl 2,3-O-isopropylidene-β-D-erythro-furanosidyl)>-1-aza-7-oxa-4-thiadioxybicyclo<3.2.1>octane
  参考文献：
  名称：

  Homochiral cycloadducts derived from sugar aldoximes via nitrone intermediates

  摘要：

  Tandem nitrone generation/cycloaddition reactions between simple sugar aldoximes and divinyl sulphone in refluxing toluene have been shown to occur regiospecifically and with high diastereoselectivity in the cycloaddition step to afford homochiral cycloadducts in good yield. The process is applicable to both furanose and pyranose aldoximes. Absolute stereochemistries of the products have been determined by NOE spectroscopy and X-ray crystallography.

  DOI：

  10.1016/s0040-4020(01)80704-3
• 作为产物：
  描述：

  (3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde 在 盐酸羟胺 作用下， 以 吡啶 、 甲醇 、 水 为溶剂， 以72%的产率得到methyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanose oxime
  参考文献：
  名称：

  Homochiral cycloadducts derived from sugar aldoximes via nitrone intermediates

  摘要：

  Tandem nitrone generation/cycloaddition reactions between simple sugar aldoximes and divinyl sulphone in refluxing toluene have been shown to occur regiospecifically and with high diastereoselectivity in the cycloaddition step to afford homochiral cycloadducts in good yield. The process is applicable to both furanose and pyranose aldoximes. Absolute stereochemistries of the products have been determined by NOE spectroscopy and X-ray crystallography.

  DOI：

  10.1016/s0040-4020(01)80704-3

文献信息

• Carbocyclic ring closure of hex-5-enopyranosides and pent-4-enofuranosides: a nitrile oxide approach
  作者：John K. Gallos、Theocharis V. Koftis

  DOI：10.1039/b007654f

  日期：——

  Nitrile oxide cycloadditions to protected enopyrano(furano)sides derived from D-glucose and D-ribose afford spiro-isoxazolines in good yield and high diastereoselectivity, which upon Raney Nickel hydrogenation in MeOH–AcOH (6∶1) undergo N–O bond cleavage followed by spontaneous aldol-like condensation to give good yields of hydroxylated six- and five-membered cyclic enaminones as the main products

  一氧化氮 衍生自受保护的依诺吡喃（呋喃）侧的环加成 d葡萄糖 和 D-核糖 可以提供高收率和高非对映选择性的螺-异恶唑啉，这在Raney Nickel上 氢化 在 甲醇-AcOH（6 ：1）进行N-O键裂解，然后自发形成类似羟醛的缩合反应，从而获得良好的羟基化六元和五元环烯胺 作为主要产品。