Hepta-O-benzoyl-hydroxycellobial | 75414-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Hepta-O-benzoyl-hydroxycellobial
• 英文别名: 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1,5-anhydro-D-arabino-hex-1-enitol；[(2R,3R,4S)-4,5-dibenzoyloxy-3-[(2S,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-2-yl]methyl benzoate
• CAS: 75414-17-4
• 化学式: C₆₁H₄₈O₁₇
• 分子量: 1053.04
• InChiKey: KPCMMPUBNQWHIY-FCQPZMPFSA-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：

  Hepta-O-benzoyl-hydroxycellobial 在 甲醇 、 3 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成
  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：

  hepta-O-benzoyl-α-D-cellobiosyl bromide 在 二乙胺 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以89%的产率得到Hepta-O-benzoyl-hydroxycellobial
  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。
• Selective deacylation of enol esters with hydroxylamine
  作者：Frieder W. Lichtenthaler、Pan Jarglis

  DOI：10.1016/s0040-4039(00)92736-9

  日期：——
• 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：——
• Lichtenthaler, Frieder W.; Roenninger, Stephan; Jarglis, Pan, Liebigs Annalen der Chemie, 1989, p. 1153 - 1162
  作者：Lichtenthaler, Frieder W.、Roenninger, Stephan、Jarglis, Pan

  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.