3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside

• 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-α-D-arabino-hexopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside
• 英文别名: 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose；(3aR,5R,6S,6aR)-6-[(2R,4R,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• 化学式: C₃₉H₄₈O₁₀
• 分子量: 676.804
• InChiKey: GDTKLYMXXVDZJO-ISPCNMFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  49
• 可旋转键数：
  13
• 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
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3,4,6-三苄氧基-D-葡萄烯糖 在 palladium on activated charcoal 三氟甲磺酸酐 、 2,4-di(tert-butyl)-4-methylpyridine 、 4 A molecular sieve 、 ammonium acetate 、 氢气 、 三苯基膦氢溴酸盐 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranosyl-(1->3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside
  参考文献：
  名称：

  1-（2'-羧基）苄基2-脱氧糖苷在直接构建2-脱氧糖基键中作为糖基供体的双重立体选择性。

  摘要：

  DOI：

  10.1002/anie.200390139

文献信息

• Reactions of Nucleophiles with Reactive Intermediates in the 3,4,6‐Tri‐<i>O</i>‐benzyl‐<scp>d</scp>‐glucal–TfOH–<i>n</i>‐Bu₄NI Reaction System
  作者：Idil Kasuto Kelson、Ben‐Ami Feit

  DOI：10.1081/car-120026596

  日期：2003.12.31

  unique reactive intermediate formed in the 3,4,6‐tri‐O‐benzyl‐d‐glucal–TfOH (triflic acid)–n‐Bu4NI reaction system (in dichloromethane) reacted with nucleophiles in a regio‐ and stereoselective manner. These selectivities resulted in hitherto unknown compounds, such as benzyl 4,6‐di‐O‐benzyl‐2,3‐dideoxy‐3‐iodo‐α‐glucopyranoside, which was obtained in the presence of an iodide ion as a nucleophile. The

  形成在3,4,6-三-独特的反应性中间ö苄基d -glucal-TfOH（三氟甲磺酸） - ñ -Bu 4 NI反应体系（在二氯甲烷中）与亲核试剂在一个区域选择性和立体选择性的方式反应。这些选择性导致了迄今未知的化合物，例如在有碘离子作为亲核试剂的情况下获得的苄基4,6-二-O-苄基-2,3-二脱氧-3-碘-α-吡喃葡萄糖苷。相应的2-脱氧α-糖苷仅在与羟基亲核试剂的相应反应中获得。
• Glycosylation with glycosyl benzyl phthalates as a new type of glycosyl donorElectronic supplementary information (ESI) available: Spectroscopic and analytical data for all new compounds. See http://www.rsc.org/suppdata/ob/b4/b405793g/
  作者：Kwan Soo Kim、Yong Joo Lee、Hye Young Kim、Sung Soo Kang、Soon Young Kwon

  DOI：10.1039/b405793g

  日期：——

  A glucopyranosyl benzyl phthalate, two mannopyranosyl benzyl phthalates, and a 2-deoxyglucopyranosyl benzyl phthalate, which were prepared from the corresponding 1-hydroxy sugars and benzyl hydrogen phthalate, were found to be efficient glycosyl donors in the glycosylations of various glycosyl acceptors using TMSOTf as a promoter.

  一种葡萄糖吡喃苯基邻苯二甲酸酯、两种甘露糖吡喃苯基邻苯二甲酸酯和一种2-脱氧葡萄糖吡喃苯基邻苯二甲酸酯是通过相应的1-羟基糖和苯基氢邻苯二甲酸酯制备的，它们被发现是TMSOTf作为促进剂时在多种糖苷受体的糖苷化反应中高效的糖苷供体。
• 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。
• 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。