3,6-dideoxy-3,6-imino-1,2-O-isopropylidene-α-D-glucofuranose | 84730-25-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-dideoxy-3,6-imino-1,2-O-isopropylidene-α-D-glucofuranose
• 英文别名: (1S,2R,6R,8S,9S)-4,4-dimethyl-3,5,7-trioxa-11-azatricyclo[6.3.0.02,6]undecan-9-ol
• CAS: 84730-25-6
• 化学式: C₉H₁₅NO₄
• 分子量: 201.222
• InChiKey: OLQVCNYHLZIYHB-TVNFTVLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  14
• 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：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,6-dideoxy-3,6-imino-1,2-O-isopropylidene-α-D-glucofuranose 在 吡啶 、 Dowex AG-5- X₈ 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 50.5h， 生成 1,2,5-tri-O-acetyl-3,6<(benzyloxycarbonyl)imino>-3,6-dideoxy-1,2-O-isopropylidene-D-glucofuranose
  参考文献：
  名称：

  Digitoxigenin 3-O-.beta.-D-furanosides

  摘要：

  The syntheses of the title compounds were accomplished by Koenig-Knorr condensation of acylated furanoses with digitoxigenin followed by basic hydrolysis of protecting groups. In this manner the riboside, 5-amino-5-deoxyriboside, 3,6-anhydroglucoside, and 3,6-dideoxy-3,6-iminoglucoside of digitoxigenin were prepared. These compounds as well as several of the synthetic intermediates showed weak to moderate cardiotonic activity.

  DOI：

  10.1021/jm00152a012
• 作为产物：
  描述：

  3-amino-3-deoxy-6-O-toluene-p-sulphonyl-1,2-O-isopropylidene-α-D-glucofuranose 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 3,6-dideoxy-3,6-imino-1,2-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Digitoxigenin 3-O-.beta.-D-furanosides

  摘要：

  The syntheses of the title compounds were accomplished by Koenig-Knorr condensation of acylated furanoses with digitoxigenin followed by basic hydrolysis of protecting groups. In this manner the riboside, 5-amino-5-deoxyriboside, 3,6-anhydroglucoside, and 3,6-dideoxy-3,6-iminoglucoside of digitoxigenin were prepared. These compounds as well as several of the synthetic intermediates showed weak to moderate cardiotonic activity.

  DOI：

  10.1021/jm00152a012

文献信息

• Reduction of 1,2;5,6-di-O-isopropylidene-α-d-glucofuranose derivatives with lithium aluminium hydride; a facile syntehtic method for 3,6-imino derivatives
  作者：Masahide Yamada、Kohichi Tachibana、Toshio Kuroda、Tohru Sakakibara

  DOI：10.1016/0008-6215(83)88284-6

  日期：1983.2

  3-acylamido- or alkylimino-3-deoxy-1,2;5,6-di- O -isopropylidene-α- d -glucofuranose with lithium aluminum hydride in boiling 1,4-dioxane afforded unusual products, namely, 3,6- N -alkylimino-3,6-dideoxy-1,2- O -isopropylidene-α- d -glucofuranose or 6- O -isopropyl-1,2- O -isopropylidene-α- d -glucofuranose derivatives. 3,6- N -(Benzyloxy)imino-3,6-dideoxy-1,2- O -isopropylidene-β- l -idofuranose, a

  摘要在沸腾的1,4-二恶烷中用氢化铝锂处理3-酰氨基-或烷基亚氨基-3-脱氧-1,2; 5,6-二-O-异亚丙基-α-d-葡萄糖呋喃糖可得到不同寻常的产物，即3，6-N-烷基亚氨基-3，6-二氧-1,2-O-异亚丙基-α-d-葡糖呋喃糖或6-O-异丙基-1,2-O-异亚丙基-α-d-葡糖呋喃糖衍生物。通过该反应，制备了3，6-N-（苄氧基）亚氨基-3，6-二脱氧-1,2-O-异亚丙基-β-1-异呋喃糖，其是合成茴香霉素的关键中间体。