(2S)-2-deoxy-2-(2'-hydroxyethyl)-4,5;7,8-di-O-isopropylidene-α-D-manno-3,6-furanoso-3-octulosonate-1,2'-lactone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-2-deoxy-2-(2'-hydroxyethyl)-4,5;7,8-di-O-isopropylidene-α-D-manno-3,6-furanoso-3-octulosonate-1,2'-lactone
• 英文别名: (3S)-3-[(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]oxolan-2-one
• 化学式: C₁₆H₂₄O₈
• 分子量: 344.362
• InChiKey: FSLRKZSJKMOVRS-KDQXRFIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• 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：

  α-溴-γ-丁内酯 、 2,3:5,6-二-O-异亚丙基-D-甘露糖酸-1,4-内酯 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 以55%的产率得到(2S)-2-deoxy-2-(2'-hydroxyethyl)-4,5;7,8-di-O-isopropylidene-α-D-manno-3,6-furanoso-3-octulosonate-1,2'-lactone
  参考文献：
  名称：

  碘化sa介导的Dreiding-Schmidt反应和sa辅助的imamoto反应使醛糖内酯的链扩展

  摘要：

  前所未有的SmI 2介导的Dreiding-Schmidt反应分别用于醛糖内酯与丙烯酸2-溴甲基丙烯酸酯或2-溴甲基丙烯腈的链增长反应。在sa粉存在下，醛糖内酯与二碘甲烷的反应导致形成聚羟基烷基取代的环丙醇。

  DOI：

  10.1016/0040-4020(96)00508-x

文献信息

• Chain extension of aldonolactones by samarium iodide mediated Dreiding-Schmidt reactions and samarium assisted imamoto reactions
  作者：René Csuk、Ulrike Höring、Martina Schaade

  DOI：10.1016/0040-4020(96)00508-x

  日期：1996.7

  Unprecedented SmI2 mediated Dreiding-Schmidt reactions were used for chain extension reactions of aldonolactones with alkyl 2-bromomethyl acrylates or 2-bromomethyl-acrylonitrile, respectively. The reaction of aldonolactones with diiodomethane in the presence of samarium powder resulted in the formation of polyhydroxyalkyl substituted cyclopropanols.

  前所未有的SmI 2介导的Dreiding-Schmidt反应分别用于醛糖内酯与丙烯酸2-溴甲基丙烯酸酯或2-溴甲基丙烯腈的链增长反应。在sa粉存在下，醛糖内酯与二碘甲烷的反应导致形成聚羟基烷基取代的环丙醇。
• Synthesis of α-substituted 3-ulosonic acids from aldonolactones
  作者：René Csuk、Ulrike Franke (nee Höring)、Zhong Hu、Claus Krieger

  DOI：10.1016/j.tet.2003.08.014

  日期：2003.9

  Zinc–silver/graphite mediated Reformatsky-reaction of furanoid aldonolactones with α-bromo-esters allows the synthesis of α-substituted 3-ulosonic acids in high yields.

  锌-银/石墨介导的呋喃类阿糖内酯与α-溴代酸酯的Reformatsky反应可合成高产率的α-取代的3-磺酸。
• 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.