1,1,2,3,4,5,6-hepta-O-acetylaldehydo-D-glucose aldehydrol | 10356-82-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,1,2,3,4,5,6-hepta-O-acetylaldehydo-D-glucose aldehydrol
• 英文别名: 1,1',2,3,4,5,6-hepta-O-acetyl-aldehydo-D-glucose hydrate；1,1,2,3,4,5,6-hepta-O-acetyl-aldehydo-D-glucose hydrate；1-acetoxy-hexa-O-acetyl-D-glucitol；1-Acetoxy-hexa-O-acetyl-D-glucit；1,1-Diacetoxy-2,3,4,5,6-penta-O-acetyl-D-glukose；D-Glucose-heptaacetat；[(2R,3R,4S,5R)-2,3,4,5,6,6-hexaacetyloxyhexyl] acetate
• CAS: 10356-82-8；118380-74-8；17296-20-7
• 化学式: C₂₀H₂₈O₁₄
• 分子量: 492.434
• InChiKey: VDDHMTHDOZEEHK-AKHDSKFASA-N

物化性质

• 沸点：
  512.4±50.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  34
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  184
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  乙酸乙烯酯 、 1,1,2,3,4,5,6-hepta-O-acetylaldehydo-D-glucose aldehydrol 在 三氟化硼乙醚 、 mercury(II) oxide 作用下， 以 溶剂黄146 为溶剂， 生成 1,1-diacetoxy-hexa-O-acetyl-D-glycero-D-gulo-1,2-dideoxy-octitol
  参考文献：
  名称：

  Zhdanov,Yu.A. et al., Journal of general chemistry of the USSR, 1968, vol. 38, p. 2533 - 2536

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4,5,6-penta-O-acetyl-D-glucose diethyl acetal 在 Dowex 50-X₂ 、 硫酸 作用下， 以 溶剂黄146 为溶剂， 反应 25.5h， 生成 1,1,2,3,4,5,6-hepta-O-acetylaldehydo-D-glucose aldehydrol
  参考文献：
  名称：

  Sulfuric acid-catalyzed acetolysis of anomeric ethyl 2,3,4,6-tetra-O-acetyl-d-glucopyranosides: kinetics and mechanism

  摘要：

  Kinetics of the acetolysis and concomitant anomerization of ethyl 2,3,4,6-tetra-O-acetyl-alpha- and -beta-D-glucopyranosides in a mixture of acetic anhydride, acetic acid, and sulfuric acid have been studied. The progress of the reactions was followed by gas chromatography, and the rate constants of the partial reactions were calculated on the basis of the time-dependent product distributions obtained. The mechanisms of the reactions are discussed.

  DOI：

  10.1016/0008-6215(95)00271-5

文献信息

• Studies on enolization of aldehydo-aldose derivatives
  作者：Stephen J. Eitelman、Derek Horton

  DOI：10.1016/j.carres.2006.08.009

  日期：2006.11

  Acetylation of the 2,3-O-isopropylidene derivative (1) of D-glyceraldehyde with hot acetic anhydride in the presence of sodium acetate give a mixture of (Z)- and (E)-enol acetates (2 and 3), together with the acetylated racemic aldehydrol (4) of 1. Likewise, the acyclic aldehydo 2,3:4,5-diisopropylidene acetals of D- and L-arabinose, D-xylose, and D-ribose underwent conversion into enol acetates, with

  在乙酸钠存在下，将D-甘油醛的2,3-O-异亚丙基衍生物（1）与热乙酸酐乙酰化，得到（Z）-和（E）-烯醇乙酸酯（2和3）的混合物乙酰化外消旋乙醛（4）为1。同样，D-和L-阿拉伯糖，D-木糖和D-核糖的无环2,3：4,5-二异亚丙基缩醛经转化为烯醇乙酸酯， （Z）异构体占优势，并且可光化学转化为相应的（E）异构体。在其他乙酰化条件下，醛衍生物被转化为相应的醛氢二乙酸酯。
• Two-Step Synthesis of Per-<i>O</i>-acetylfuranoses: Optimization and Rationalization
  作者：Rémy Dureau、Laurent Legentil、Richard Daniellou、Vincent Ferrières

  DOI：10.1021/jo201913f

  日期：2012.2.3

  A simple two-step procedure yielding peracetylated furanoses directly from free aldoses was implemented. Key steps of the method are (i) highly selective formation of per-O-(tert-butyldimethylsilyl)furanoses and (ii) their clean conversion into acetyl ones without isomerization. This approach was easily applied to galactose and structurally related carbohydrates such as arabinose, fucose, methyl galacturonate

  实现了一个简单的两步程序，直接从游离醛糖中产生过乙酰化呋喃糖酶。该方法的关键步骤是（i）高选择性形成过-O-（叔丁基二甲基甲硅烷基）呋喃糖和（ii）在不异构化的情况下将其干净地转化为乙酰基。这种方法很容易应用于半乳糖和与结构相关的碳水化合物，例如阿拉伯糖，岩藻糖，半乳糖醛酸甲酯和N-乙酰半乳糖胺得到相应的过乙酰化目标。该方法的成功取决于至少三个参数的控制：（i）起始未保护糖的互变异构平衡，（ii）靶向呋喃糖酶和甲硅烷基化剂的空间位阻，最后，（iii）保护基相互转化期间的每个软亲核试剂。
• A facile one-pot procedure for the transformation of acetonides into diacetates catalyzed with Bi(OTf)3·xH2O
  作者：Qin-Pei Wu、Ming-Xin Zhou、Xiao-Dong Xi、Di Song、Yuan Wang、Hai-Xia Liu、Yun-Zheng Li、Qing-Shan Zhang

  DOI：10.1016/j.tetlet.2008.02.163

  日期：2008.4

  The transformation of acetonides into the corresponding diacetates is often required in the synthetic chemistry. An efficient procedure for direct conversion of acetonides into diacetates in the presence of Bi(OTf)3·xH2O under mild conditions has been developed. Primary hydroxyl-acetonides could be selectively transformed into diacetates in the presence of anomeric acetonides and the anomeric acetonides

  在合成化学中通常需要将丙酮化物转化为相应的二乙酸盐。开发了一种在温和的条件下在Bi（OTf）3 · x H 2 O存在下将丙酮化物直接转化为二乙酸盐的有效方法。可以在异头丙酮化物的存在下将伯羟基丙酮化物选择性地转化为二乙酸盐，并且异头丙酮化物可以可调谐地转化为2-乙酰氧基异丙基或二乙酸盐基团。
• Bredereck et al., Chemische Berichte, 1958, vol. 91, p. 515,522, 524
  作者：Bredereck et al.

  DOI：——

  日期：——
• Dasgupta, Falguni; Singh, Prem P.; Srivastava, Harish C., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 527 - 529
  作者：Dasgupta, Falguni、Singh, Prem P.、Srivastava, Harish C.

  DOI：——

  日期：——