1-O-benzoyl-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose | 76573-35-8

• 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: 1-O-benzoyl-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose
• 英文别名: ((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-3a-yl)methyl benzoate；[(1R,2S,6S,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-6-yl]methyl benzoate
• CAS: 76573-35-8
• 化学式: C₁₉H₂₄O₇
• 分子量: 364.395
• InChiKey: MKMSQSGWCUXMDJ-CUYVQJCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-O-benzoyl-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose 在 乙醇 、 草酸 作用下， 生成 O¹-Benzoyl-D-fructose
  参考文献：
  名称：

  The Constitution of Inulin. Synthesis of 3,4,6- and 1,4,6-Trimethyl-γ-fructose

  摘要：

  DOI：

  10.1021/ja01317a042
• 作为产物：
  描述：

  3-苯基丙基苯甲酸酯 在 bis(1,5-cyclooctadiene)nickel (0) 、 potassium tert-butylate 、 3-(2,6-diisopropylphenyl)-1-(2-pyridyl)imidazolium bromide 、 1,2-双(二环己基磷基)-乙烷 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 1-O-benzoyl-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose
  参考文献：
  名称：

  镍催化甲酯的酯交换反应

  摘要：

  使用 Ni/dcype 催化开发了甲酯与脂肪醇的酯交换反应。该反应的特点是在没有酸性或碱性添加剂的情况下强 C(酰基)-OMe 键的断裂，产生挥发性甲醇作为唯一的化学计量废物。多种（杂）芳香族和脂肪族甲酯可以以良好到优异的收率和高效率转化为相应的官能化酯。与传统的酯交换反应相比，这种交叉偶联方法为高效和化学选择性合成提供了新的机会。

  DOI：

  10.1055/s-0042-1751485

文献信息

• Electrochemical Nickel‐Catalyzed Hydrogenation
  作者：Liubo Li、Xinyi Wang、Niankai Fu

  DOI：10.1002/anie.202403475

  日期：——

  efficient electrochemical Ni-catalyzed alkene hydrogenation is described. The reaction features outstanding substrate generality and functional group compatibility, and distinct chemoselectivity. Notably, hydrodebromination of alkyl and aryl bromides can be realized using the same reaction system with a different ligand, and high chemoselectivity between hydrogenation of alkene and hydrodebromination could

  描述了一种经济有效的电化学镍催化烯烃加氢反应。该反应具有出色的底物通用性和官能团兼容性以及独特的化学选择性。值得注意的是，烷基溴和芳基溴的加氢脱溴可以使用相同的反应体系和不同的配体来实现，并且通过配体的选择可以实现烯烃加氢和加氢脱溴之间的高化学选择性。
• 3-(Dimethylamino)-1-propylamine: A Cheap and Versatile Reagent for Removal of Byproducts in Carbohydrate Chemistry
  作者：Sofie Meng Andersen、Mads Heuckendorff、Henrik H. Jensen

  DOI：10.1021/acs.orglett.5b00041

  日期：2015.2.20

  Inexpensive 3-(dimethylamino)-1-propylamine (DMAPA) was found to be effective in anomeric deacylation reactions giving 1-O deprotected sugars in high yield as precursors for the formation of imidate glycosyl donors. DMAPA was also found to be useful for removing excess reagents such as benzoyl chloride, tosyl chloride, and 2,2,2-trifluoro-N-phenylacetimidoyl chloride. The deacylation reaction could be conducted in moist THF and did not require chromatographic purification since an acidic wash was sufficient to remove excess reagent and the formed byproduct.
• Szeja, Wieslaw, Polish Journal of Chemistry, 1980, vol. 54, # 6, p. 1301 - 1304
  作者：Szeja, Wieslaw

  DOI：——

  日期：——
• The Constitution of Inulin. Synthesis of 3,4,6- and 1,4,6-Trimethyl-γ-fructose
  作者：T. N. Montgomery

  DOI：10.1021/ja01317a042

  日期：1934.2
• Acyl chloride/DABCO-promoted acetal migration of 1,2:4,5-di-O-isopropylidene-d-fructopyranose
  作者：Xiang-Bao Meng、Yun-Feng Li、Zhong-Jun Li

  DOI：10.1016/j.carres.2007.02.005

  日期：2007.6

  An unprecedented acetal migration was observed when 1,2:4,5-di-O-isopropylidene-D-fructose was treated with various acyl chlorides and 1,4-diaza-bicyclo [2.2.2]octane (DABCO). 2,3:4,5-Di-O-isopropylidene-D-fructose derivatives were isolated as the only product in high to quantitative yields. The acylium cations generated in situ were speculated as the electrophilic species to initiate the migration process. (c) 2007 Elsevier Ltd. All rights reserved.