6-O-acetyl-1,2,3,5-bis(O-methylidene)-α-D-glucofuranose | 32448-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 6-O-acetyl-1,2,3,5-bis(O-methylidene)-α-D-glucofuranose
• 英文别名: 6-O-acetyl-1,2:3,5-di-O-methylene-α-D-glucofuranose；O⁶-acetyl-O¹,O²;O³,O⁵-dimethanediyl-α-D-glucofuranose；O⁶-Acetyl-O¹,O²;O³,O⁵-dimethandiyl-α-D-glucofuranose；6-O-Acetyl-1,2:3,5-di-o-methylidene-alpha-d-glucofuranose；[(1S,2R,6R,8R,9R)-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecan-9-yl]methyl acetate
• CAS: 32448-00-3
• 化学式: C₁₀H₁₄O₇
• 分子量: 246.217
• InChiKey: MCEITQNVODJCRI-SPFKKGSWSA-N

物化性质

• 沸点：
  339.7±37.0 °C(Predicted)
• 密度：
  1.311±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-O-acetyl-1,2,3,5-bis(O-methylidene)-α-D-glucofuranose 在 lithium aluminium tetrahydride 、 sodium 、 sodium hydride 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 20.0h， 生成 1,2:3,5-bis(O-methylidene)-6-O-(2'-hydroxyethyl)-α-D-glucofuranose
  参考文献：
  名称：

  4-O-和6-O-（2'-碘乙基）-d-葡萄糖的合成

  摘要：

  摘要将1,2,3,6-四-O-乙酰基-d-吡喃葡萄糖进行O-烯丙基化，然后进行臭氧化/还原反应，得到4-羟乙基衍生物。还使用烷基化/还原序列从1,2：3,5-双（O-亚甲基）-α-d-葡糖呋喃糖开始在C-6处引入该羟乙基取代基。然后通过碘化然后脱保护将这些4-和6-O-羟乙基衍生物转化为标题化合物。值得注意的是，这些醚中的碳碘键具有特殊的稳定性，这是其在单光子发射计算机断层扫描医学成像（SPECT）中潜在使用的前提。

  DOI：

  10.1016/s0008-6215(98)00180-3
• 作为产物：
  描述：

  1,2:3,5-bis(O-methylidene)-α-D-glucofuranose 在 吡啶 、 potassium acetate 、 乙酸酐 作用下， 生成 6-O-acetyl-1,2,3,5-bis(O-methylidene)-α-D-glucofuranose
  参考文献：
  名称：

  Schmidt et al., Chemische Berichte, 1953, vol. 86, p. 741,743

  摘要：

  DOI：

文献信息

• A chromatographic and mass-spectrometric study of 6-O-(2- hydroxyethyl)-D-glucose and its ethylene oxide adducts
  作者：Olle Ramnäs、Olof Samuelson

  DOI：10.1016/s0008-6215(00)81458-5

  日期：1968.3

  and its ethylene oxide adducts having 2–5 ethylene oxide units in the 6-position, were synthesised, and separated by partition chromatography on an anion-exchange resin. Paper chromatography, gas-liquid chromatography, and mass spectrometry were used in the characterisation of these compounds.

  摘要合成了6-O-（2-羟乙基）-D-葡萄糖及其在6-位具有2-5个环氧乙烷单元的环氧乙烷加合物，并通过在阴离子交换树脂上的分配色谱法进行了分离。纸色谱，气液色谱和质谱法用于表征这些化合物。
• THE STRUCTURE OF MONO-<i>O</i>-METHYLENEAND DI-<i>O</i>-METHYLENE-<scp>D</scp>-GLUCOSE
  作者：W. P. Shyluk、John Honeyman、T. E. Timell

  DOI：10.1139/v55-143

  日期：1955.7.1

  The structure of 1,2-O-methylene-α-D-glucofuranose has been proved by preparing the 3,5,6-trimethanesulphonate and the 3,5,6-tri-p-toluenesulphonate derivatives of this compound from the corresponding derivatives of 1,2-O-iso-propylidene-α-D-glucofuranose. The results also constitute an additional proof for the recently established structure of the 1,2;3,5-di-O-methylene-α-D-gluco-furanose.

  1,2-O-甲基糠醛的结构已经通过制备该化合物的3,5,6-三甲磺酸盐和3,5,6-三对甲苯磺酸盐衍生物，从相应的1,2-O-异丙基糠醛衍生物中证明。这些结果还为最近确定的1,2;3,5-二-O-甲基糠醛的结构提供了额外的证明。
• 524. Sugar nitrates. Part V. Removal of nitrate groups
  作者：K. S. Ennor、John Honeyman

  DOI：10.1039/jr9580002586

  日期：——
• Glucofuranose derivatives as a library for designing and investigating low molecular mass organogelators
  作者：Roman Luboradzki、Zbigniew Pakulski、Bożena Sartowska

  DOI：10.1016/j.tet.2005.07.093

  日期：2005.10

  We designed and synthesized a class of saccharide-based gelators having three free OH groups in the glucofuranose fragment. The gelating abilities of fourteen compounds were examined to systematically study the influence of the hydrophobic fragment connected to the C2' carbon. Also the correlation between the saccharide crystal structure and its gelating properties was examined, showing limited usefulness in this particular case. SEM observations were carried out in order to investigate the hierarchical structure of xerogels and changes depending on different gel concentration. (c) 2005 Elsevier Ltd. All rights reserved.
• Hough et al., Journal of the Chemical Society, 1952, p. 1525
  作者：Hough et al.

  DOI：——

  日期：——