3-O-benzyl-4-O-tert-butyldimethylsilyl-2,6-dideoxy-β-D-ribohexapyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside | 1512846-75-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-benzyl-4-O-tert-butyldimethylsilyl-2,6-dideoxy-β-D-ribohexapyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside
• 英文别名: tert-butyl-dimethyl-[(2R,3R,4S,6R)-2-methyl-4-phenylmethoxy-6-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-3-yl]oxysilane
• CAS: 1512846-75-1
• 化学式: C₃₁H₅₀O₉Si
• 分子量: 594.818
• InChiKey: OGOFQHYWDGOPFY-VZPARZTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1,5-anhydro-3-O-benzyl-4-O-(tert-butyldimethylsilyl)-2,6-dideoxy-D-ribo-hex-1-enitol 、 双丙酮半乳糖 在 [ReOCl3(OPPh3)(SMe2)] 作用下， 以 苯 为溶剂， 反应 12.0h， 以62.264%的产率得到
  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