p-bromophenyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: p-bromophenyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• 英文别名: [(2R,3S,6S)-3-acetyloxy-6-(4-bromophenyl)-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• 化学式: C₁₆H₁₇BrO₅
• 分子量: 369.212
• InChiKey: BIXWYYYJUWSHTF-HRCADAONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-溴苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 四丁基氯化铵 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.67h， 生成 p-bromophenyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  钯（II）催化与二芳基碘鎓盐从糖中立体合成C-糖苷

  摘要：

  描述了有效的钯（II）介导的二芳基碘鎓盐对糖的C-糖基化，为合成具有优异立体选择性的2,3-二脱氧C-芳基糖苷提供了新的策略。所述Ç不同范围的烯糖的-glycosylation，包括d -glucal，d -galactal，d -allal，大号-rhamnal，大号-fucal，大号-arabinal，d -maltal，和d -lactal，有效地发生，并且相应的C-β-糖苷以中等至良好的产率获得。由于丰富的官能团相容性，广泛的底物范围和出色的α-立体选择性，该方案被认为是对碳水化合物化学领域的重要补充。

  DOI：

  10.1039/d0ob00247j

文献信息

• Palladium-Catalyzed Stereoselective<i>C</i>-Glycosylation of Glycals with Sodium Arylsulfinates
  作者：Jimei Ma、Shaohua Xiang、Hong Jiang、Xue-Wei Liu

  DOI：10.1002/ejoc.201403550

  日期：2015.2

  An efficient glycosylation method to synthesize 2-deoxy-C-aryl glycosides was developed. This C-glycosylation strategy is based on a palladium-catalyzed desulfitative Ferrier-type coupling reaction of glycals and sodium arylsulfinates. A series of C-aryl glycosides were obtained in moderate to good yields with exclusive regio- and stereoselectivities. The anomeric selectivity was found to depend on

  开发了一种有效的糖基化方法来合成 2-脱氧-C-芳基糖苷。这种 C-糖基化策略基于钯催化的糖基和芳基亚磺酸钠的脱硫 Ferrier 型偶联反应。以中等至良好的收率获得了一系列 C-芳基糖苷，具有独特的区域和立体选择性。发现异头选择性取决于聚糖的 C3 取代基的构型。
• Desulfitative<i>C</i>-Arylation of Glycals by Using Benzenesulfonyl Chlorides
  作者：Anil Kumar Kusunuru、Syed Khalid Yousuf、Madhubabu Tatina、Debaraj Mukherjee

  DOI：10.1002/ejoc.201403195

  日期：2015.1

  The palladium-catalyzed stereoselective synthesis of 2,3-deoxy-C-aryl glycosides was investigated. The strategy is based on the Pd-catalyzed desulfitative Heck coupling of arylsulfonyl chlorides and glycals with good leaving groups. An attempt was made to establish the reaction mechanism, which may involve PdII/Pd0 interconversion under basic conditions.

  研究了钯催化的 2,3-脱氧-C-芳基糖苷的立体选择性合成。该策略基于具有良好离去基团的芳基磺酰氯和糖醛的 Pd 催化脱硫 Heck 偶联。尝试建立可能涉及碱性条件下 PdII/Pd0 互变的反应机制。
• Synthesis of alkyl and aryl C-pyranosides using organozinc reagents via a Ferrier-type rearrangement
  作者：Song Xue、Lin He、Kai-Zhen Han、Xiao-Qi Zheng、Qing-Xiang Guo

  DOI：10.1016/j.carres.2004.11.012

  日期：2005.2

  diethylzinc and diphenylzinc in the presence of CF3COOH gave the corresponding alky and aryl C-pyranosides via a Ferrier rearrangement in excellent yields. Use of the organozinc species, CF3CO2ZnPh, reacted with high stereoselectivity to give the phenyl C-glycosides. Arylzinc chlorides could also be successfully applied to this reaction in the presence of BF3.OEt2.

  在CF 3 COOH的存在下，乙酸1，2-二氢吡喃基乙酸酯与二甲基锌，二乙基锌和二苯基锌的反应通过Feer重排以优异的产率得到了相应的烷基和芳基C-吡喃糖苷。使用有机锌物质CF3CO2ZnPh以高立体选择性反应生成苯基C-糖苷。在BF3.OEt2存在下，芳基氯化锌也可成功应用于该反应。
• Oxidative Heck Reaction of Glycals and Aryl Hydrazines: A Palladium-Catalyzed <i>C</i>-Glycosylation
  作者：Yaguang Bai、Le Mai Hoang Kim、Hongze Liao、Xue-Wei Liu

  DOI：10.1021/jo401032r

  日期：2013.9.6

  An efficient Heck-type C-glycosylation of glycals via the C-N bond cleavage of aryl hydrazines has been developed. The flexibility of the reaction was tested by the substrate scope, consisting of glycals from different carbohydrate origins as well as aryl hydrazines with various substituents. Pure alpha-C-glycosides were obtained when (3R)-glycals were employed, whereas alpha,beta mixtures were observed with (3S)-glycals.