1,2-isopropylidene-α-D-gluco-hexodialdo-1,4-furanose | 25531-72-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 1,2-isopropylidene-α-D-gluco-hexodialdo-1,4-furanose
• 英文别名: 1.2-O-Isopropyliden-α-D-gluco-hexodialdo-1.4-furanose；(1S,2R,6R,8R,9S)-4,4-dimethyl-3,5,7,11-tetraoxatricyclo[6.3.0.02,6]undecane-9,10-diol
• CAS: 25531-72-0；74006-22-7；74006-23-8
• 化学式: C₉H₁₄O₆
• 分子量: 218.207
• InChiKey: VVJYBHBRDBGWPD-AASYGJKBSA-N

物化性质

• 沸点：
  354.1±42.0 °C(Predicted)
• 密度：
  1.419±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• 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：

  1,2-isopropylidene-α-D-gluco-hexodialdo-1,4-furanose 、 苄胺 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 6-benzylamino-O¹,O²-isopropylidene-6-deoxy-α-D-glucofuranose
  参考文献：
  名称：

  Concise and practical route to tri- and tetra-hydroxy seven-membered iminocyclitols as glycosidase inhibitors from d-(+)-glucurono-γ-lactone

  摘要：

  An efficient and short total synthesis of tetrahydroxy-1c and trihydroxy-azepane id is reported in 72% and 57% overall yields, respectively, from D-(+)-glucurono-gamma-lactone. Thus, D-glucuronolactone 2 on acetonide protection. DIBAL-H reduction and one-pot intermolecular reductive amination followed by -NCbz protection afforded 6-(N-benzyl-N-benzyloxycarbonyl) amino-6-deoxy-1,2-O-isopropylidene-alpha-D-gluco-1,4-furanose 5a. 1,2-Acetonide hydrolysis in 5a and Pd-mediated intramolecular reductive aminocyclization afforded tetrahydroxyazepane 1c. An analogous pathway with 5-deoxy-1,2-O-isopropylidene-alpha-D-glucurono-6,3-lactone 3b gave trihydroxy-azepane id. Glycosidase inhibitory activity of 1c/1d was studied and id was found to be potent inhibitor of alpha-mannosidase and beta-galactosidase. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.060
• 作为产物：
  描述：

  1,2-O-异亚丙基-D-呋喃葡萄糖 在 [RuH2(PPh3)4] 苯亚甲基苯乙酮 作用下， 以 various solvent(s) 为溶剂， 反应 24.0h， 生成 1,2-isopropylidene-α-D-gluco-hexodialdo-1,4-furanose
  参考文献：
  名称：

  Détermination des sites d'oxydation des dérivés du α-D-glucofuranose utilisés comme donneurs

  摘要：

  DOI：

  10.1016/s0008-6215(00)83657-5

文献信息

• Détermination des sites d'oxydation des dérivés du α-D-glucofuranose utilisés comme donneurs
  作者：Gérard Descotes、Denis Sinou、Jean-Pierre Praly

  DOI：10.1016/s0008-6215(00)83657-5

  日期：1980.1
• Concise and practical route to tri- and tetra-hydroxy seven-membered iminocyclitols as glycosidase inhibitors from d-(+)-glucurono-γ-lactone
  作者：Navnath B. Kalamkar、Vijay M. Kasture、Sanjay T. Chavan、Sushma G. Sabharwal、Dilip D. Dhavale

  DOI：10.1016/j.tet.2010.08.060

  日期：2010.10

  An efficient and short total synthesis of tetrahydroxy-1c and trihydroxy-azepane id is reported in 72% and 57% overall yields, respectively, from D-(+)-glucurono-gamma-lactone. Thus, D-glucuronolactone 2 on acetonide protection. DIBAL-H reduction and one-pot intermolecular reductive amination followed by -NCbz protection afforded 6-(N-benzyl-N-benzyloxycarbonyl) amino-6-deoxy-1,2-O-isopropylidene-alpha-D-gluco-1,4-furanose 5a. 1,2-Acetonide hydrolysis in 5a and Pd-mediated intramolecular reductive aminocyclization afforded tetrahydroxyazepane 1c. An analogous pathway with 5-deoxy-1,2-O-isopropylidene-alpha-D-glucurono-6,3-lactone 3b gave trihydroxy-azepane id. Glycosidase inhibitory activity of 1c/1d was studied and id was found to be potent inhibitor of alpha-mannosidase and beta-galactosidase. (C) 2010 Elsevier Ltd. All rights reserved.