ethyl (5R)-5-[(1R)-1,2-dihydroxyethyl]-4,5-dihydro-1,2-oxazole-3-carboxylate | 104048-47-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: ethyl (5R)-5-[(1R)-1,2-dihydroxyethyl]-4,5-dihydro-1,2-oxazole-3-carboxylate
• CAS: 104048-47-7；104048-48-8
• 化学式: C₈H₁₃NO₅
• 分子量: 203.195
• InChiKey: WNPSLRVWOTXDIQ-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  88.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5R-5-(1,2-O-cyclohexylidene-D-glycero-diitol-1-yl)-3-ethoxycarbonyl-4,5-dihydroisoxazole 在 溶剂黄146 作用下， 反应 2.0h， 以80%的产率得到ethyl (5R)-5-[(1R)-1,2-dihydroxyethyl]-4,5-dihydro-1,2-oxazole-3-carboxylate
  参考文献：
  名称：

  Stereoselective cycloaddition of nitrile oxides to a dispiroketal-protected but-3-ene-1,2-diol

  摘要：

  The influence of a dispiroketal protecting group on the pi-facial selectivity of nitrile oxide cycloaddition to S-but-3-ene-1,2-diol has been investigated Ethoxycarbonylformonitrile oxide and benzonitrile oxide undergo regiospecific and diasteroeselective addition to alkene 7 to afford isoxazolines 11 and 12. The major adducts (11a and 11b) are formed with 44% and 50% d.e. respectively, and in each case have S-configuration at C-5, the new stereogenic centre.

  DOI：

  10.1016/0957-4166(95)00362-s

文献信息

• Silyl nitronates and nitrile oxides in organic synthesis. A novel route to d,l-deoxysugars. Use of aluminum oxide as solid phase base for generation of
  作者：K.B.G. Torssell、A.C. Hazell、R.G. Hazell

  DOI：10.1016/s0040-4020(01)91358-4

  日期：1985.1

  to a diene. 2. Stereospecific hydroxylation of the double bond. 3. Unmasking of the aldol moiety by catalytic reduction of the 2-isoxazoline. The syntheses of D,L-deoxyribose, D,L-oleose, D,L-digitoxose, D,L-2-deoxygalactose, 1,3-dideoxyfructose, 3-deoxyfructose etc. are described. Basic aluminum oxide is introduced as a solid phase base for the one step synthesis of 2-isoxazolines from aldoximes and

  为脱氧醛糖和脱氧酮糖的三步合成开发了新的方法：1.选择性地将亚硝酸甲硅烷基酯或氧化亚氮区域选择性地加成到二烯中。2.双键的立体特异性羟基化。3.通过催化还原2-异恶唑啉使醛醇部分不掩盖。描述了D，L-脱氧核糖，D，L-油糖，D，L-指氧糖，D，L-2-脱氧半乳糖，1，3-二脱氧果糖，3-脱氧果糖的合成。引入碱性氧化铝作为固相碱，用于由醛肟和烯烃一步合成2-异恶唑啉。化合物的X射线衍射研究验证了立体化学分配。
• Stereoselective osmylation of 5-vinyl-4,5-dihydroisoxazoles
  作者：Rita Annunziata、Mauro Cinquini、Franco Cozzi、Laura Raimondi

  DOI：10.1039/c39850000403

  日期：——

  Osmium tetroxide-catalysed cis-hydroxylation of 5-vinyl-4,5-dihydroisoxazoles proceeds stereoselectively affording the anti-products in fair to excellent diastereoisomeric excess; an entry to optically active compounds is also described.

  四氧化催化的5-乙烯基-4,5-二氢异恶唑的顺式羟化反应可立体选择性地进行，从而提供反产物，其反义异构体过量至极好的非对映异构体过量；还描述了旋光化合物的入口。