hexa-O-acetyl-aldehydo-D-xylose aldehydrol | 34168-70-2

• 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: hexa-O-acetyl-aldehydo-D-xylose aldehydrol
• 英文别名: D-1-acetoxy-penta-O-acetyl-xylitol；D-1-Acetoxy-penta-O-acetyl-xylit；Hexa-O-acetyl-aldehydo-D-xylose；Hexaacetylxylose；[(2R,3S,4R)-2,3,4,5,5-pentaacetyloxypentyl] acetate
• CAS: 34168-70-2
• 化学式: C₁₇H₂₄O₁₂
• 分子量: 420.37
• InChiKey: PCWVNHHXSDHRDP-OWCLPIDISA-N

物化性质

• 沸点：
  454.1±45.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  29
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  158
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 hexa-O-acetyl-aldehydo-D-xylose aldehydrol
  参考文献：
  名称：

  醛-D-半乳糖七乙酸酯和醛-D-木糖六乙酸酯形成瓜兰和木聚糖的乙酰分解。

  摘要：

  DOI：

  10.1021/ja01172a095

文献信息

• The influence of boric acid on the acetylation of aldoses: ‘one-pot’ syntheses of penta-O-acetyl-β-D-glucofuranose and its crystalline propanoyl analogue
  作者：Richard H. Furneaux、Phillip M. Rendle、Ian M. Sims

  DOI：10.1039/b002841j

  日期：——

  When glucose and boric acid are heated in acetic acid a soluble compound forms from which, with acetic anhydride and catalytic amounts of sulfuric acid, a mixture consisting of >90% of the glucofuranose per-acetates (α∶β ratio 1∶1.8) is obtained in high yield. In the absence of the sulfuric acid partial acetylation takes place and penta-O-acetyl-β-D-glucofuranose (α∶β ratio 1∶52) is obtainable in good yield by removal of boric acid and completion of the esterification by addition of acetic anhydride and pyridine. A new, crystalline glucofuranose, penta-O-propanoyl-β-D-glucofuranose, is obtained in 58% yield in a ‘one-pot’ procedure using boric acid. The effects of boric acid on the acid-catalysed acetylation of other aldo-hexoses and -pentoses suggest that the synthesis of furanosyl per-esters could be successful with xylose and idose as well as with glucose. p

  当葡萄糖和硼酸在醋酸中加热时，会形成一种可溶性化合物，从中通过醋酐和少量的硫酸催化，可以获得含有>90%的葡萄呋喃糖全乙酸酯（α∶β比率为1∶1.8）的高产率混合物。在没有硫酸的情况下，会发生部分乙酰化，通过去除硼酸并加入醋酐和吡啶完成酯化反应，可以以良好的产率获得五-O-乙酰基-β-D-葡萄呋喃糖（α∶β比率为1∶52）。通过使用硼酸的“一锅法”程序，可以以58%的产率获得一种新的结晶葡萄呋喃糖，即五-O-丙酸酰基-β-D-葡萄呋喃糖。 硼酸对其他己醛糖和戊醛糖的酸催化乙酰化反应的影响表明，与葡萄糖一样，木糖和艾杜糖的呋喃糖全酯合成也可能是成功的。
• The preparation and properties of peracetylated -xylo-oligosaccharides with all residues in the aldehydrol form
  作者：Ashoke Banerjee、Brian Capon

  DOI：10.1016/s0040-4020(01)85420-x

  日期：1990.1

  Acetolysis of xylan with acetic anhydride, acetic acid and sulphuric acid yields hexa-0-acetyl-aldehydo-D- xylose aldehydrol and a series of related peracetylated oligosaccharides with the xylose residues in the acyclic form. These were characterised by their 1H and 13 C-n.m.r. spectra, their mass spectra and by Zemplen deacetylation when they yielded D-xylose.

  用乙酸酐，乙酸和硫酸的产率六木聚糖的乙酰解0乙酰基醛基-D-木糖aldehydrol和一系列与所述非环形式的木糖残基相关的全乙酰寡糖。它们的特征在于它们的1 H和13 Cn.mr光谱，它们的质谱以及当它们产生D-木糖时的Zemplen脱乙酰化作用。
• Acetylation of carbohydrates using ferric chloride in acetic anhydride
  作者：Falguni Dasgupta、Prem P. Singh、Harish C. Srivastava

  DOI：10.1016/s0008-6215(00)84876-4

  日期：1980.4
• Pirie, Biochemical Journal, 1936, vol. 30, p. 374
  作者：Pirie

  DOI：——

  日期：——