1,6-Anhydro-β-D-mannohexofuranose | 31880-33-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 1,6-Anhydro-β-D-mannohexofuranose
• 英文别名: 1,6-anhydro-β-D-mannofuranose；1,6-Anhydro-β-D-mannofuanose；1,6-Anhydro-beta-D-mannofuranose；(1R,4R,5R,6R,7S)-2,8-dioxabicyclo[3.2.1]octane-4,6,7-triol
• CAS: 31880-33-8
• 化学式: C₆H₁₀O₅
• 分子量: 162.142
• InChiKey: GYNYBVOAJFHCRG-VFUOTHLCSA-N

物化性质

• 熔点：
  185-188 °C(Solv: methanol (67-56-1); ethyl acetate (141-78-6))
• 沸点：
  416.5±45.0 °C(Predicted)
• 密度：
  1.688±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,6-Anhydro-β-D-mannohexofuranose 、 对甲苯磺酰氯 在 吡啶 作用下， 反应 140.0h， 以79%的产率得到1,6-Anhydro-5-O-tosyl-β-D-mannofuranose
  参考文献：
  名称：

  Koell, Peter; Komander, Herbert; Meyer, Bernd, Liebigs Annalen der Chemie, 1984, # 9, p. 1591 - 1596

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl α-D-mannofuranoside 以 环丁砜 为溶剂， 反应 0.5h， 以48.5%的产率得到1,6-Anhydro-β-D-mannohexofuranose
  参考文献：
  名称：

  Synthesis, Characterization, and Lectin Recognition of Hyperbranched Polysaccharide Obtained from 1,6-Anhydro-d-hexofuranose

  摘要：

  1,6-Anhydro-D-hexofuranoses, such as 1,6-anhydro-beta-D-glucofuranose (1), 1,6-anhydro-beta-D-mannofuranose (2), and 1,6-anhydro-alpha-D-galactofuranose (3), were polymerized using a thermally induced cationic catalyst in dry propylene carbonate to afford hyperbranched polysaccharides (poly1-3) with degrees of branching from 0.40 to 0.46. The weight-average molecular weights of polyl - 3 measured by multiangle laser light scattering varied in the range from (1.02 to 5.84) x 10(4) g.mol(-1), which were significantly higher than those measured by size exclusion chromatography. The intrinsic viscosities ([eta]) of poly1 - 3 were very low in the range from 4.9 to 7.4 mL.g(-1). The exponent (alpha) in the Mark-Houkwink-Sakurada equation ([eta] = KM(alpha)) of the polymers was 0.20 to 0.33, which is < 0.5. The steady shear flow of poly1 - 3 in an aqueous solution exhibited a Newtonian behavior with steady shear viscosities independent of the shear rate. These viscosity characteristics were attributed to the spherical structures of hyperbranched polysaccharides in an aqueous solution. Poly1 - 3 contained a high portion of terminal units of 31-43 mol % nonreducing D-hexopyranosyl and D-hexofuranosyl units, in which the D-hexofuranosyl units were 20-44 mol %. Moreover, polyl and poly2 showed a strong interaction to Concanavalin A due to the cluster effect or multivalent effect of numerous nonreducing saccharide units on their surfaces with binding constants in the range from 1.7 x 10(4) to 2.7 x 10(5) M(-1).

  DOI：

  10.1021/bm2002413

文献信息

• Selective synthesis of 1,6-anhydro-β-d-mannopyranose and -mannofuranose using microwave-assisted heating
  作者：Nguyen To Hoai、Akiyoshi Sasaki、Masahide Sasaki、Harumi Kaga、Toyoji Kakuchi、Toshifumi Satoh

  DOI：10.1016/j.carres.2011.05.032

  日期：2011.9

  The dehydration of D-mannose and the demethanolization of methyl-alpha-D-mannopyranoside (M alpha MP) or methyl-alpha-D-mannofuranoside (M alpha MF) were examined using microwave-assisted heating for a 3-min irradiation at temperature from 120 to 280 degrees C in ordinary or dry sulfolane without any catalyst. The microwave-assisted heating of MaMP and M alpha MF smoothly proceeded to selectively afford the anhydromannoses, 1,6-anhydro-beta-D-mannopyranose (AMP) and 1,6-anhydro-beta-D-mannofuranose (AMF), respectively, in high yields. For MaMP in ordinary sulfolane at 240 degrees C, AMP was selectively obtained in the AMF: AMP ratio of 4: 96, whereas AMF was the major product at the AMF: AMP ratio of 97: 3 from M alpha MF in dry sulfolane at 220 degrees C. (C) 2011 Elsevier Ltd. All rights reserved.