(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside | 79384-23-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside
• CAS: 79384-23-9
• 化学式: C₃₉H₄₈O₁₀
• 分子量: 676.804
• InChiKey: GDTKLYMXXVDZJO-SVGYNYBKSA-N

物化性质

• 沸点：
  722.8±60.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  49.0
• 可旋转键数：
  13.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  92.3
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  Dithiocarbonic acid O-{(2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[(3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-tetrahydro-pyran-3-yl} ester S-methyl ester 在 2,2'-azobisbutyronitrile 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 生成 (3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside
  参考文献：
  名称：

  Gurjar, M. K.; Ghosh, P. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 1063 - 1064

  摘要：

  DOI：

文献信息

• Reagent-Controlled Stereoselective Glycosylation
  申请人：Trustees of Tufts College

  公开号：US20150038689A1

  公开（公告）日：2015-02-05

  Provided are methods for the efficient stereoselective formation of glycosidic bonds, without recourse to prosthetic or directing groups.

  提供了一种高效立体选择性形成糖苷键的方法，无需使用假体或定向基团。
• Facile O-glycosylation of glycals using Glu-Fe₃O₄-SO₃H, a magnetic solid acid catalyst
  作者：Raju S. Thombal、Vrushali H. Jadhav

  DOI：10.1039/c6ra03305a

  日期：——

  A new glucose derived magnetic solid acid catalyst (Glu-Fe3O4-SO3H) was synthesized in a convenient and ecofriendly manner and well characterized using FTIR, PXRD, EDAX, SEM, and XPS which showed the presence of Fe3O4 embedded on the surface of the catalyst along with –SO3H, –OH and –COOH functional groups. This new heterogeneous catalyst was studied for synthesis of 2-deoxy galactosides/glucosides

  以方便，环保的方式合成了一种新型的葡萄糖衍生磁性固体酸催化剂（Glu-Fe 3 O 4 -SO 3 H），并通过FTIR，PXRD，EDAX，SEM和XPS对其进行了很好的表征，表明存在Fe 3 O 4与–SO 3 H，–OH和–COOH官能团一起嵌入催化剂表面。研究了这种新型多相催化剂，用于合成2-脱氧半乳糖苷/葡糖苷，具有良好的收率和选择性。而且，催化剂可以容易地用外磁力从反应中分离出来，并至少可重复使用四次，而每次循环后产物的产率没有任何明显的降低。
• A Reagent-Controlled S_N2-Glycosylation for the Direct Synthesis of β-Linked 2-Deoxy-Sugars
  作者：John Paul Issa、Clay S. Bennett

  DOI：10.1021/ja500410c

  日期：2014.4.16

  of the reaction cannot be controlled using the stereochemical information intrinsic to the glycosyl donor. Here we show that p-toluenesulfonic anhydride activates 2-deoxy-sugar hemiacetals in situ as electrophilic species, which react stereoselectively with nucleophilic acceptors to produce β-anomers exclusively. NMR studies confirm that, under these conditions, the hemiacetal is quantitatively converted

  糖苷键的有效和立体选择性构建仍然是有机化学中最艰巨的挑战之一。在 β 连接的脱氧糖等情况下尤其如此，在这种情况下，无法使用糖基供体固有的立体化学信息来控制反应结果。在这里，我们表明对甲苯磺酸酐原位激活 2-脱氧糖半缩醛作为亲电物质，其与亲核受体立体选择性地反应以专门产生 β-端基异构体。NMR 研究证实，在这些条件下，半缩醛被定量转化为 α-甲苯磺酸糖基酯，这可能是反应中的活性物质。
• Glycosyloxyselenation–deselenation of glycals: a new approach to 2′-deoxy-disaccharides
  作者：Guy Jaurand、Jean-Marie Beau、Pierre Sinay

  DOI：10.1039/c39810000572

  日期：——

  Glycopsyloxyselenation of 3,4,6-tri-O-benzyl-D-glucal followed by reductive removal of the phenylseleno-group demonstrates the poetential of a novel synthetic approach to 2′-deoxy-disaccharides.

  3,4,6-三-O-苄基-D-葡糖醛糖基糖基化，然后还原性去除苯基硒基，证明了合成2'-脱氧-二糖的新方法的潜力。
• Catalytic stereoselective synthesis of 2-deoxy α-glycosides using glycosyl <i>ortho</i>-[1-(<i>p</i>-MeOPhenyl)Vinyl]Benzoate (PMPVB) donors
  作者：Suvendu Halder、Rupa Bai Addanki、Bikash K. Sarmah、Pavan K. Kancharla

  DOI：10.1039/d1ob02502c

  日期：——

  2-Deoxy glycosyl ortho-[1-(p-MeOPhenyl)Vinyl]Benzoates (PMPVB) have been presented as stable, reactive glycosyl donors for the synthesis of 2-deoxy α-glycosides. The donors react under Brønsted acid conditions to provide the 2-deoxy-α-glycosides with very high stereocontrol. The observed high stereoselectivities were discussed with respect to the relative free energy differences between the anomeric

  2-脱氧糖基邻-[1-( p -MeOPhenyl)Vinyl]Benzoates (PMMPB) 已被用作合成 2-脱氧 α-糖苷的稳定、反应性糖基供体。供体在 Brønsted 酸条件下反应以提供具有非常高立体控制的 2-脱氧-α-糖苷。就异头反应中间体之间的相对自由能差异讨论了观察到的高立体选择性。