ethyl 2-deoxy-4,5:7,8-di-O-isopropyliden-2,2-dimethyl-α-D-manno-3,6-furanoso-3-octulosonate | 1207346-51-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-deoxy-4,5:7,8-di-O-isopropyliden-2,2-dimethyl-α-D-manno-3,6-furanoso-3-octulosonate
• 英文别名: ethyl 2-[(3aS,4S,6R,6aS)-6-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-hydroxy-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl]-2-methylpropanoate
• CAS: 1207346-51-7
• 化学式: C₁₈H₃₀O₈
• 分子量: 374.431
• InChiKey: JNFASVCESRJDMA-HUJGMYITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-溴-2-甲基丙酸乙酯 、 2,3:5,6-二-O-异亚丙基-D-甘露糖酸-1,4-内酯 在 indium 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl 2-deoxy-4,5:7,8-di-O-isopropyliden-2,2-dimethyl-β-D-manno-3,6-furanoso-3-octulosonate 、 ethyl 2-deoxy-4,5:7,8-di-O-isopropyliden-2,2-dimethyl-α-D-manno-3,6-furanoso-3-octulosonate
  参考文献：
  名称：

  铟介导的内酯的Reformatsky反应：2-脱氧-2,2'-二甲基-3-乌磺酸的制备

  摘要：

  单纯的内酯和醛糖内酯与α-溴代异丁酸乙酯的铟介导的Reformatsky反应可分别以高收率合成相应的缩酮和乌酸酯。

  DOI：

  10.1016/j.tetlet.2009.10.092

文献信息

• Studies on indium-mediated additions to lactones: synthesis of 2-deoxy-2-substituted-3-ulosonic acids
  作者：Raquel G. Soengas

  DOI：10.1016/j.tetasy.2010.07.011

  日期：2010.9

  The indium-mediated Reformatsky reaction of a mannose-derived lactone with alpha,alpha-disubstituted-alpha-bromo esters yielded the corresponding ulosonic acid esters as mixtures of anomers. In contrast, the reaction with alpha-monosubstituted-alpha-bromo esters is highly stereoselective and afforded a single anomer of the corresponding (2S)-ulosonic acid esters. A mechanistic proposal for the reaction and an explanation of its outcome is discussed. The indium-mediated Reformatslcy reaction of the mannose-derived lactone with 2-bromo-lactones was also achieved and the products obtained were consistent with those of our proposed mechanism in all cases. Moreover, indium-mediated allylation of the model sugar lactone was also investigated. (C) 2010 Elsevier Ltd. All rights reserved.
• Indium-mediated Reformatsky reaction on lactones: preparation of 2-deoxy-2,2′-dimethyl-3-ulosonic acids
  作者：Raquel G. Soengas

  DOI：10.1016/j.tetlet.2009.10.092

  日期：2010.1

  Indium-mediated Reformatsky reactions of simple lactones and aldonolactones with ethyl α-bromoisobutyrate allow the synthesis of the corresponding ketals and ulosonic acid esters, respectively, in good yields.

  单纯的内酯和醛糖内酯与α-溴代异丁酸乙酯的铟介导的Reformatsky反应可分别以高收率合成相应的缩酮和乌酸酯。