1,5-anhydro-2,3,4-tri-O-benzoyl-6-deoxy-D-arabino-hex-1-enitol | 52080-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,5-anhydro-2,3,4-tri-O-benzoyl-6-deoxy-D-arabino-hex-1-enitol
• 英文别名: 3,4-di-O-benzoyl-2-benzoyloxy-6-deoxy-D-glucal；[(2R,3R,4S)-4,5-dibenzoyloxy-2-methyl-3,4-dihydro-2H-pyran-3-yl] benzoate
• CAS: 52080-34-9
• 化学式: C₂₇H₂₂O₇
• 分子量: 458.467
• InChiKey: XZUKJEHUMVFOHK-DQMJNTIXSA-N

物化性质

• 沸点：
  600.5±35.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-2,3,4-tri-O-benzoyl-6-deoxy-D-arabino-hex-1-enitol 在 盐酸 、 4 A molecular sieve 、 silver alumosilicate reagent 、 氯 、 乙酰氯 作用下， 以 水 、 甲苯 为溶剂， 反应 16.25h， 生成
  参考文献：
  名称：

  A concise, stereocontrolled synthesis of spectinomycin

  摘要：

  A simple and concise synthesis of the antibiotic spectinomycin is described. The key step comprises a reaction cascade initiated by the P-selective 5-O-glycosylation of an N,N-blocked myo-1,3-inosadiamine 10 with a suitable actinospectosyl donor-the D-glucose-derived enol benzoate of 4,6-dideoxy-alpha-D-hex-3-enulosyl chloride 5 - which is spontaneously followed by regio- and stereospecific cyclohemiketalization and a 3-O -> 2-O-benzoyl group migration to directly elaborate the cis cisoid-trans-fused pyran-dioxane-cyclohexane framework of 1. The approach is flexible enough to be applied to other inosadiamines towards the generation of novel spectinomycin analogues. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.03.035

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。
• A convenient access to 1,5-anhydroketoses
  作者：F.W. Lichtenthaler、E.S.H. El Ashry、V.H. Göckel

  DOI：10.1016/s0040-4039(00)92737-0

  日期：——

  A convenient, versatile entry into the 1,5-anhyroketose series is described and their conversion into enolones, enolone oximes and γ-pyrones.

  描述了一种方便，通用的进入1,5-脱水酮糖系列的方法，并将其转换为烯醇酮，烯醇酮肟和γ-吡喃酮。
• 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：——
• A Concise and General Method for Doubly Attaching 2-Ketosugars to Aglycon Diols: Synthesis of the Gomphosides and Spectinomycin
  作者：Frieder W. Lichtenthaler、Eckehard Cuny、Osamu Sakanaka

  DOI：10.1002/anie.200500434

  日期：2005.8.5