2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1,5-anhydro-D-arabino-hex-1-enitol | 87760-36-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1,5-anhydro-D-arabino-hex-1-enitol
• 英文别名: Hepta-O-benzoyl-hydroxylactal；2,3,6-tri-O-benzoyl-4-O-(2,3,4,5-tetra-O-benzoyl-β-D-galactopyranosyl)-1,5-anhydro-D-arabino-hex-1-enitol；[(2R,3R,4S)-4,5-dibenzoyloxy-3-[(2S,3R,4S,5S,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate
• CAS: 87760-36-9
• 化学式: C₆₁H₄₈O₁₇
• 分子量: 1053.04
• InChiKey: KPCMMPUBNQWHIY-DVLNWHQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  78
• 可旋转键数：
  25
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.16
• 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-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1,5-anhydro-D-arabino-hex-1-enitol 在 吡啶 、 2,4,6-三甲基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 3 A molecular sieve 、 盐酸羟胺 、 碘 、 一水合肼 、 1,1,3,3-四甲基脲 作用下， 以 1,4-二氧六环 、 四氯化碳 、 乙醇 、 水 为溶剂， 反应 74.5h， 生成 methyl hexa-O-benzoyl-α-D-lactosuloside oxime
  参考文献：
  名称：

  Disaccharide-derived 2-oxo- and 2-oximinoglycosyl bromides: novel, conveniently accessible building blocks for the expedient construction of oligosaccharides with .alpha.-D-glucosamine, .beta.-D-mannose, and .beta.-D-mannosamine as constituent sugars

  摘要：

  DOI：

  10.1021/jo00219a017
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->4)-1,2,3,6-tetra-O-benzoyl-D-glucopyranose 在 氢溴酸 、 二乙胺 、 sodium iodide 作用下， 以 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 反应 40.25h， 生成 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-1,5-anhydro-D-arabino-hex-1-enitol
  参考文献：
  名称：

  Disaccharide-derived 2-oxo- and 2-oximinoglycosyl bromides: novel, conveniently accessible building blocks for the expedient construction of oligosaccharides with .alpha.-D-glucosamine, .beta.-D-mannose, and .beta.-D-mannosamine as constituent sugars

  摘要：

  DOI：

  10.1021/jo00219a017

文献信息

• Various Glycosyl Donors with a Ketone or Oxime Function next to the Anomeric Centre: Facile Preparation and Evaluation of their Selectivities in Glycosidations
  作者：Frieder W. Lichtenthaler、Ulrich Kläres、Matthias Lergenmüller、Sabine Schwidetzky

  DOI：10.1055/s-1992-34167

  日期：——

  An efficient one-pot procedure is described for the conversion of a variety of hydroxyglycal esters to their 2-oxoglycosyl bromides which simply comprises of brief treatment with N-bromosuccinimide/methanol at ambient temperature. Exhibiting comparably low anomeric reactivity in glycosidation reactions, these ulosyl bromides, as well as their 2-benzoyloxyimino analogs, can readily be transformed into a range of more reactive glycosyl donors with iodine, pentenyloxy, ethylthio and dithiocarbamoyl residues at the anomeric centre, such that any ß-selective glycosidation may be successfullv achieved.

  描述了一种高效的一锅法步骤，用于将多种羟基甘油酯转化为其2-氧基糖苷溴化物，该过程仅涉及在室温下用N-溴琥珀酰亚胺/甲醇进行简短处理。这些氧基糖苷溴化物在糖苷化反应中表现出相对较低的异构体反应性，同时，它们的2-苯甲氧羰基亚氨基类似物也可以很容易地转化为一系列更具反应性的糖苷供体，这些供体在异构体中心具有碘、戊烯氧、乙硫基和二硫氨基甲酰基残基，从而可以成功实现任何β选择性的糖苷化反应。
• Sodium hydride/hexamethylphosphoric triamide: a new and efficient reagent towards the synthesis of protected 1,2- and 5,6-enopyranosides
  作者：Khalid Mohammed Khan、Shahnaz Perveen、Syed Tasadaque Ali Shah、Mohammed Saleh Shekhani、Wolfgang Voelter

  DOI：10.1039/b010196f

  日期：——

  A new method for the elimination of hydrogen halides and p-toluenesulfonic acid from sugar moieties using sodium hydride (NaH) in hexamethylphosphoric triamide (HMPA) at room temperature is reported. NaH/HMPA has several advantages compared to NaH/DMF: elimination products are produced in high yields even from sterically hindered starting materials, and not only from halides, but also tosylates.

  消除...的新方法 卤化氢 和 对甲苯磺酸 从糖部分使用 氢化钠 （NaH）在 六甲基磷酸三酰胺报告了室温下的（HMPA）。与NaH / DMF相比，NaH / HMPA具有多个优点：消除产物即使从位阻起始原料中也不仅从卤化物，也可以甲苯磺酸盐。
• A Method for the Syntheses of Enopyranosides
  作者：Khalid Khan、Shahnaz Perveen、Raed Al-Qawasmeh、Mohammed Shekhani、Syed Ali Shah、Wolfgang Voelter

  DOI：10.2174/157017809787893109

  日期：2009.4.1

  Sodium hydride (NaH) in hexamethylphosphoric triamide (HMPA) has been introduced as an economical and efficient reagent towards the creation of 1,2- or 5,6-enopyranosides from the corresponding halogenated or tosylated pyranosides. NaH/HMPA has several advantages compared to NaH/DMF: elimination products are produced in high yields even from sterically-hindered halides as well as tosylates.

  六甲基磷酸三酰胺（HMPA）中的氢化钠（NaH）作为一种经济、高效的试剂被引入到从相应的卤代或对甲苯磺酰基吡喃糖苷生成 1,2- 或 5,6- 烯吡喃糖苷的过程中。与 NaH/DMF 相比，NaH/HMPA 具有以下几个优点：即使从立体受阻的卤化物和对甲苯磺酸盐中也能生成高产率的消除产物。
• Lichtenthaler, Frieder W.; Cuny, Eckehard; Weprek, Sabine, Angewandte Chemie, 1983, vol. 95, # 11, p. 906 - 908
  作者：Lichtenthaler, Frieder W.、Cuny, Eckehard、Weprek, Sabine

  DOI：——

  日期：——
• Convenient access to 4-O-glycosylated 1,5-anhydro-d-fructoses via disaccharide-derived 2-hydroxyglycal esters
  作者：Toshio Nakagawa、Frieder W. Lichtenthaler

  DOI：10.1016/j.tetasy.2011.03.005

  日期：2011.4

  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.