tert-butyl-[(2R,3R,4S,6S)-3-[(4-methoxyphenyl)methoxy]-2-methyl-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-4-yl]oxy-dimethylsilane | 1512846-78-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl-[(2R,3R,4S,6S)-3-[(4-methoxyphenyl)methoxy]-2-methyl-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-4-yl]oxy-dimethylsilane
• CAS: 1512846-78-4
• 化学式: C₃₂H₅₂O₁₀Si
• 分子量: 624.844
• InChiKey: QXZWJZGFUBWWBK-MJXMRFLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  1,5-anhydro-4-O-p-methoxybenzyl-D-ribo-hex-1-enitol 在 咪唑 、 [ReOCl3(OPPh3)(SMe2)] 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 13.0h， 生成 3-O-tert-butyldimethylsilyl-2,6-dideoxy-4-O-p-methoxybenzyl-β-D-ribohexapyranosyl-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 、 tert-butyl-[(2R,3R,4S,6S)-3-[(4-methoxyphenyl)methoxy]-2-methyl-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-4-yl]oxy-dimethylsilane
  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.