(2R,3S,4R)-4-(benzyloxy)-2-((benzyloxy)methyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydro-2H-pyran-5-carbaldehyde | 296268-58-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R)-4-(benzyloxy)-2-((benzyloxy)methyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydro-2H-pyran-5-carbaldehyde
• 英文别名: 3,6,2',3',4',6'-hexa-O-benzyl-2-C-formyl-D-lactal；(2R,3S,4R)-4-phenylmethoxy-2-(phenylmethoxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carbaldehyde
• CAS: 296268-58-1
• 化学式: C₅₅H₅₆O₁₀
• 分子量: 877.044
• InChiKey: VPILACDHLOQMSH-HPPHWGOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  65
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  甲基三苯基溴化膦 、 (2R,3S,4R)-4-(benzyloxy)-2-((benzyloxy)methyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydro-2H-pyran-5-carbaldehyde 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.17h， 以74%的产率得到
  参考文献：
  名称：

  Glycosidation of 3,4,6-Tri-O-Benzyl-2-Ethenyl-D-Glucal – A Route to 2-C-(β-Methyl)Methylene Glycosides

  摘要：

  Monosaccharidic and disaccharidic 2-C-(beta-methyl)methylene glycosides were synthesized by an electrophilic conjugate addition reaction of ROH-type compounds in the presence of Ph3+PH Br- to 2-ethenyl-3,4,6-tri-O-benzyl-D-glucal 1, functioning as a model glycosyl donor. This 2-vinyl glucal derivative represents a series of 2-vinyl, and 2-butadienyl glycals, prepared by Wittig-type methylenation of pyranosidic conjugated enals, derived from glucal, galactal and lactal. The exo-(beta-methyl)methylene group paves the way for further chemical transformations.

  DOI：

  10.1080/07328300008544109
• 作为产物：
  描述：

  hexa-O-benzyl lactal 、 N,N-二甲基甲酰胺 在 ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate 作用下， 反应 18.0h， 以56%的产率得到(2R,3S,4R)-4-(benzyloxy)-2-((benzyloxy)methyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-tetrahydro-2H-pyran-2-yl)oxy)-3,4-dihydro-2H-pyran-5-carbaldehyde
  参考文献：
  名称：

  X talFluor-E在C -2-甘醇的Vilsmeier-Haack甲酰化反应中作为POCl 3的替代物

  摘要：

  我们报告了在C -2-糖的Vilsmeier-Haack甲酰化反应中使用XtalFluor-E（[Et 2 NSF 2 ] BF 4）作为POCl 3的替代物。使用XtalFluor-E / DMF组合可以以11–90％的产率分离出所需的C -2-甲酰基乙二醇。此方法扩展到一个合成C- 2 -甲酰化二糖烯糖。

  DOI：

  10.1021/acs.joc.8b01006

文献信息

• Glycosidation of 3,4,6-Tri-<i>O</i>-Benzyl-2-Ethenyl-D-Glucal – A Route to 2-<i>C</i>-(β-Methyl)Methylene Glycosides
  作者：Ben-Ami Feit、Idil Kasuto Kelson、Anke Gerull、Sarah Abramson、Richard R. Schmidt

  DOI：10.1080/07328300008544109

  日期：2000.1

  Monosaccharidic and disaccharidic 2-C-(beta-methyl)methylene glycosides were synthesized by an electrophilic conjugate addition reaction of ROH-type compounds in the presence of Ph3+PH Br- to 2-ethenyl-3,4,6-tri-O-benzyl-D-glucal 1, functioning as a model glycosyl donor. This 2-vinyl glucal derivative represents a series of 2-vinyl, and 2-butadienyl glycals, prepared by Wittig-type methylenation of pyranosidic conjugated enals, derived from glucal, galactal and lactal. The exo-(beta-methyl)methylene group paves the way for further chemical transformations.
• Use of XtalFluor-E as an Alternative to POCl₃ in the Vilsmeier–Haack Formylation of <i>C</i>-2-Glycals
  作者：Majdouline Roudias、Frédéric Vallée、Julien Martel、Jean-François Paquin

  DOI：10.1021/acs.joc.8b01006

  日期：2018.8.3

  We report the use of XtalFluor-E ([Et2NSF2]BF4) as an alternative to POCl3 in the Vilsmeier–Haack formylation reaction of C-2-glycals. Employing a XtalFluor-E/DMF combination allowed the desired C-2-formyl glycals to be isolated in 11–90% yield. This method was extended to the synthesis of a C-2-formylated disaccharide glycal.

  我们报告了在C -2-糖的Vilsmeier-Haack甲酰化反应中使用XtalFluor-E（[Et 2 NSF 2 ] BF 4）作为POCl 3的替代物。使用XtalFluor-E / DMF组合可以以11–90％的产率分离出所需的C -2-甲酰基乙二醇。此方法扩展到一个合成C- 2 -甲酰化二糖烯糖。