2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1,5-anhydro-D-arabino-hex-1-enitol | 171336-45-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1,5-anhydro-D-arabino-hex-1-enitol
• 英文别名: 2,2',3,3',4',6,6'-hepta-O-acetyl-2-hydroxymaltal；2-acetoxymaltal hexaacetate；2-acetoxy-maltal peracetate；[(2R,3R,4S)-4,5-diacetyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 171336-45-1
• 化学式: C₂₆H₃₄O₁₇
• 分子量: 618.546
• InChiKey: HKHFGRYHJSJSEU-BOUKTIKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  43
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  212
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1,5-anhydro-D-arabino-hex-1-enitol 在 吡啶 、 盐酸羟胺 作用下， 反应 24.0h， 以81%的产率得到3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1,5-anhydro-D-fructose E-oxime
  参考文献：
  名称：

  Convenient access to 4-O-glycosylated 1,5-anhydro-d-fructoses via disaccharide-derived 2-hydroxyglycal esters

  摘要：

  Efficient six-step protocols are described for the conversion of common disaccharides, such as maltose, cellobiose, or lactose, into the corresponding 4-O-glycosyl-1,5-anhydro-D-fructoses. Overall yields of 40-45% are favorably compared to the alternative eleven-step procedure from their monosaccharide components (similar to 15%). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.03.005
• 作为产物：
  描述：

  2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide 在 1,5-Diazabicyclo[5.4.0]undec-5-ene 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以78%的产率得到2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1,5-anhydro-D-arabino-hex-1-enitol
  参考文献：
  名称：

  Inclusion and solubilization properties of 6-S-glycosyl-6-thio derivatives of β-cyclodextrin

  摘要：

  The synthesis and physico-chemical properties of branched beta-cyclodextrins substituted by one or seven thioglycoside units at the primary hydroxy side are described. The solubilities in water of these compounds are strongly increased compared with the parent beta-cyclodextrin although large differences are found between alpha- and beta-anomers, the former exhibiting the larger solubility. The inclusion capacity of these derivatives has been investigated using NMR spectroscopy as the major analytical technique for various host-guest pairs. The apparent discrepancies between the intrinsic solubilities of these host molecules and their ability to solubilize hydrophobic hosts can be explained from geometrical considerations derived from detailed NMR studies. The respective roles of the:side of inclusion, of steric effects and of stabilizing interactions are evidenced and allow an a priori selection of the optimal host derivative for a given guest molecule.

  DOI：

  10.1039/p29950001479

文献信息

• Stereoselective Thioconjugation by Photoinduced Thiol‐ene Coupling Reactions of Hexo‐ and Pentopyranosyl <scp>d</scp> ‐ and <scp>l</scp> ‐Glycals at Low‐Temperature—Reactivity and Stereoselectivity Study
  作者：Viktor Kelemen、Miklós Bege、Dániel Eszenyi、Nóra Debreczeni、Attila Bényei、Tobias Stürzer、Pál Herczegh、Anikó Borbás

  DOI：10.1002/chem.201903095

  日期：2019.11.18

  A comprehensive optimization and mechanistic study on the photoinduced hydrothiolation of different d- and l- hexo- and pentoglycals with various thiols was performed, at the temperature range of RT to -120 °C. Addition of thiols onto 2-substituted hexoglycals proceeded with complete 1,2-cis-α-stereoselectivity in all cases. Hydrothiolation of 2-substituted pentoglycals resulted in mixtures of 1,2-cis-α-

  在室温至-120°C的温度范围内，对不同的D-，L-己糖和戊糖与各种硫醇进行光诱导的氢硫醇化反应进行了全面的优化和机理研究。在所有情况下，将硫醇添加到2-取代的己糖上均具有完全的1,2-顺式-α-立体选择性。2-取代的戊糖的氢硫醇化作用导致1，2-顺式-α-和-β-硫代糖苷的混合物的比例取决于反应物的构型。未取代的乙二醇在-80°C的氢硫醇化反应具有优异的收率，并且除半乳糖以外，还提供了具有高选择性的轴向C2-S连接异构体。冷却总是有益于功效，增加了产率，并且在大多数情况下显着提高了立体选择性。