2,6-dideoxy-3,4-bis-O-(triethylsilyl)-β-D-ribohexapyranosyl-(1→4)-2,6-dideoxy-3-O-triethylsilyl-β-D-ribo-hexapyranosyl-(1→4)-1,5-anhydro-2,6-dideoxy-3-O-triethylsilyl-D-ribo-hex-1-enitol | 1512847-06-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-dideoxy-3,4-bis-O-(triethylsilyl)-β-D-ribohexapyranosyl-(1→4)-2,6-dideoxy-3-O-triethylsilyl-β-D-ribo-hexapyranosyl-(1→4)-1,5-anhydro-2,6-dideoxy-3-O-triethylsilyl-D-ribo-hex-1-enitol
• 英文别名: triethyl-[(2R,3R,4S,6S)-2-methyl-3-[(2S,4S,5R,6R)-6-methyl-4,5-bis(triethylsilyloxy)oxan-2-yl]oxy-6-[[(2R,3R,4S)-2-methyl-4-triethylsilyloxy-3,4-dihydro-2H-pyran-3-yl]oxy]oxan-4-yl]oxysilane
• CAS: 1512847-06-1
• 化学式: C₄₂H₈₆O₉Si₄
• 分子量: 847.481
• InChiKey: OYEFBZQEIZVAOG-WUDWAHKMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.52
• 重原子数：
  55.0
• 可旋转键数：
  24.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  83.07
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2,6-dideoxy-3,4-bis-O-(triethylsilyl)-β-D-ribohexapyranosyl-(1→4)-2,6-dideoxy-3-O-triethylsilyl-β-D-ribo-hexapyranosyl-(1→4)-1,5-anhydro-2,6-dideoxy-3-O-triethylsilyl-D-ribo-hex-1-enitol 在 氟化铵 、 三苯基膦氢溴酸盐 作用下， 以 N-甲基吡咯烷酮 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.17h， 生成 C1′-epi-digitoxin 、 洋地黄毒苷
  参考文献：
  名称：

  Catalytic Stereoselective Synthesis of β-Digitoxosides: Direct Synthesis of Digitoxin and C1′-epi-Digitoxin

  摘要：

  A mild and atom-economic rhenium(V)-catalyzed stereoselective synthesis of beta-D-digitoxosides from 6-deoxy-D-allals has been described. This beta-selective glycosylation was achieved probably because of the formation of corresponding alpha-digitoxosides disfavored by 1,3-diaxial interaction. In addition, this method has been successfully applied to the synthesis of digitoxin trisaccharide glycal for the direct synthesis of digitwdn and C1'-epi-digitoxin.

  DOI：

  10.1021/jo4021419
• 作为产物：
  描述：

  1,2,4,6-tetra-O-acetyl-3-O-benzylallopyranose 在 咪唑 、 lithium aluminium tetrahydride 、 LiDBB 、 [ReOCl3(OPPh3)(SMe2)] 、 三氟化硼乙醚 、 二苯基酸 、 四丁基氟化铵 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 190.75h， 生成 2,6-dideoxy-3,4-bis-O-(triethylsilyl)-β-D-ribohexapyranosyl-(1→4)-2,6-dideoxy-3-O-triethylsilyl-β-D-ribo-hexapyranosyl-(1→4)-1,5-anhydro-2,6-dideoxy-3-O-triethylsilyl-D-ribo-hex-1-enitol
  参考文献：
  名称：

  Catalytic Stereoselective Synthesis of β-Digitoxosides: Direct Synthesis of Digitoxin and C1′-epi-Digitoxin

  摘要：

  A mild and atom-economic rhenium(V)-catalyzed stereoselective synthesis of beta-D-digitoxosides from 6-deoxy-D-allals has been described. This beta-selective glycosylation was achieved probably because of the formation of corresponding alpha-digitoxosides disfavored by 1,3-diaxial interaction. In addition, this method has been successfully applied to the synthesis of digitoxin trisaccharide glycal for the direct synthesis of digitwdn and C1'-epi-digitoxin.

  DOI：

  10.1021/jo4021419

文献信息

• Catalytic Stereoselective Synthesis of β-Digitoxosides: Direct Synthesis of Digitoxin and C1′-epi-Digitoxin
  作者：Kedar N. Baryal、Surya Adhikari、Jianglong Zhu

  DOI：10.1021/jo4021419

  日期：2013.12.20

  A mild and atom-economic rhenium(V)-catalyzed stereoselective synthesis of beta-D-digitoxosides from 6-deoxy-D-allals has been described. This beta-selective glycosylation was achieved probably because of the formation of corresponding alpha-digitoxosides disfavored by 1,3-diaxial interaction. In addition, this method has been successfully applied to the synthesis of digitoxin trisaccharide glycal for the direct synthesis of digitwdn and C1'-epi-digitoxin.