5-O-acetyl-3,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose | 71110-17-3

• 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: 5-O-acetyl-3,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose
• 英文别名: [(1S,2R,6R,8R,9S)-4,4-dimethyl-3,5,7,11-tetraoxatricyclo[6.3.0.02,6]undecan-9-yl] acetate
• CAS: 71110-17-3
• 化学式: C₁₁H₁₆O₆
• 分子量: 244.244
• InChiKey: XUCKASMYMPWHMI-SQXHDICFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.19
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-O-acetyl-3,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose 在 吡啶 、 Dowex AG-50 X₈ 、 氨 、 氢溴酸 、 氰化汞 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 31.5h， 生成 4-(3-((3,6-dihydroxyhexahydrofuro[3,2-b]furan-2-yl)oxy)-14-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)furan-2(5H)-one
  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：

  1,2-O-isopropylidene-3-O-p-toluenesulfonyl-α-D-allofuranose 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 11.0h， 生成 5-O-acetyl-3,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose
  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

• Synthesis and reactions of chlorodeoxy-l-idofuranoid derivatives
  作者：Cheang Kuan Lee

  DOI：10.1016/0008-6215(88)85060-2

  日期：1988.6

  Synthese a partir de l'O-acetyl-3 di-O-mesyl-5,6 O-isopropylidene-1,2 α-D-glucofuranose et d'acetate ou benzoate de potassium dans du DMF

  合成L'O-乙酰基-3二-O-甲磺酰基-5,6 O-异亚丙基-1,2α-D-葡糖呋喃糖等及DMF苯甲酸钾
• LEE, CHEANG KUAN, CARBOHYDR. RES., 177,(1988) 247-252
  作者：LEE, CHEANG KUAN

  DOI：——

  日期：——