6-deoxy-1,2-O-isopropylidene-3-O-methyl-α-D-gluco-heptofuranose | 75251-58-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-deoxy-1,2-O-isopropylidene-3-O-methyl-α-D-gluco-heptofuranose
• 英文别名: (1R)-1-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]propane-1,3-diol
• CAS: 75251-58-0
• 化学式: C₁₁H₂₀O₆
• 分子量: 248.276
• InChiKey: SGIOAMAKMIGUCP-HOTMZDKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 6-deoxy-1,2-O-isopropylidene-3-O-methyl-α-D-gluco-heptofuranose 以 吡啶 为溶剂， 以88%的产率得到5,7-Di-O-acetyl-6-desoxy-1,2-O-isopropyliden-3-O-methyl-α-D-gluco-heptofuranose
  参考文献：
  名称：

  Paulsen, Hans; Stubbe, Mathias; Heiker, Fred R., Liebigs Annalen der Chemie, 1980, # 6, p. 825 - 837

  摘要：

  DOI：
• 作为产物：
  描述：

  6-Desoxy-6-(4,5-dihydro-5-methyl-1,3,5-dithiazin-2-yl)-1,2-O-isopropyliden-3-O-methyl-α-D-glucofuranose 在 sodium tetrahydroborate 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 水 、 乙腈 为溶剂， 生成 6-deoxy-1,2-O-isopropylidene-3-O-methyl-α-D-gluco-heptofuranose
  参考文献：
  名称：

  Paulsen, Hans; Stubbe, Mathias; Heiker, Fred R., Liebigs Annalen der Chemie, 1980, # 6, p. 825 - 837

  摘要：

  DOI：

文献信息

• Further Evidence for the Critical Role of a Non-Chair Conformation of L-Iduronic Acid in the Activation of Antithrombin
  作者：José Kovensky、Jean-Maurice Mallet、Jacques Esnault、Pierre-Alexandre Driguez、Philippe Sizun、Jean-Pascal Hérault、Jean-Marc Herbert、Maurice Petitou、Pierre Sinaÿ

  DOI：10.1002/1099-0690(200211)2002:21<3595::aid-ejoc3595>3.0.co;2-f

  日期：2002.11

  L-iduronic acid, a conformationally flexible monosaccharide, imparts a remarkable protein adaptability to the glycosammoglycans heparin, heparan sulfate, and dermatan sulfate. The pentasaccharide representing the antithrombin binding site of heparin contains one such L-iduronic acid residue, the conformation of which has been suspected for a long time to be a critical factor in the interaction with antithrombin. We have recently synthesized pentasaccharides containing an Liduronic acid residue conformationally forced to exist within a restricted arc (S-2(0) reversible arrow B-2,B-5 reversible arrow S-5(1)) of the overall pseudorotational circle. We could thus demonstrate that the S-2(0) conformation is adopted upon binding to the protein. In the present work, we now describe the synthesis of a similar pentasaccharide containing a slightly more flexible L-iduronic acid unit with a three-atom bridge between C-2 and C5 of the hexopyranose ring. This pentasaccharide is a better activator of AT-III with respect to blood coagulation factor Xa inhibition. These results confirm that L-iduronic acid adopts an unusual non-chair conformation close to S-2(0) and clearly explains how the unique conformational behavior Of L-iduronic acid is the key to heparin's interaction with AT-III.
• Paulsen, Hans; Stubbe, Mathias; Heiker, Fred R., Liebigs Annalen der Chemie, 1980, # 6, p. 825 - 837
  作者：Paulsen, Hans、Stubbe, Mathias、Heiker, Fred R.

  DOI：——

  日期：——