[(2R,3S,6S)-6-[[(3aR,4R,6R,6aR)-2,2-dimethyl-4-phenylmethoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy]-2-(trityloxymethyl)-3,6-dihydro-2H-pyran-3-yl] 2,2-dimethylpropanoate | 947396-51-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: [(2R,3S,6S)-6-[[(3aR,4R,6R,6aR)-2,2-dimethyl-4-phenylmethoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy]-2-(trityloxymethyl)-3,6-dihydro-2H-pyran-3-yl] 2,2-dimethylpropanoate
• CAS: 947396-51-2
• 化学式: C₄₅H₅₀O₉
• 分子量: 734.887
• InChiKey: FYYZQEKZBSZLNG-UJYBHKRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  54
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  90.9
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(2R,3S,6S)-6-[[(3aR,4R,6R,6aR)-2,2-dimethyl-4-phenylmethoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy]-2-(trityloxymethyl)-3,6-dihydro-2H-pyran-3-yl] 2,2-dimethylpropanoate 在 碳酸氢钠 Oxone 、 乙二胺四乙酸 、 1,1,1-三氟丙酮 作用下， 以 水 、 乙腈 为溶剂， 反应 3.25h， 生成
  参考文献：
  名称：

  Palladium-Catalyzed Stereoselective Formation of α-O-Glycosides

  摘要：

  [GRAPHICS]A novel method for palladium-catalyzed stereoselective formation of alpha-O-glycosides has been developed. This strategy relies on the palladium-biaryl phosphine catalyst-glycal donor complexation to control the anomeric selectivity. It does not depend on the nature of the protecting groups on the substrates, thus eliminating the need for cumbersome protecting group manipulations.

  DOI：

  10.1021/ol071268z
• 作为产物：
  描述：

  [(2R,3S,4R)-4-(2,2,2-trichloroethanimidoyl)oxy-2-(trityloxymethyl)-3,4-dihydro-2H-pyran-3-yl] 2,2-dimethylpropanoate 、 benzyl 2,3-O-isopropylidene-D-ribofuranoside 在 二(氰基苯)二氯化钯 diethylzinc 、 2,6-二叔丁基苯酚 作用下， 以 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 10.0h， 以88%的产率得到[(2R,3S,6S)-6-[[(3aR,4R,6R,6aR)-2,2-dimethyl-4-phenylmethoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy]-2-(trityloxymethyl)-3,6-dihydro-2H-pyran-3-yl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Palladium-Catalyzed Stereoselective Formation of α-O-Glycosides

  摘要：

  [GRAPHICS]A novel method for palladium-catalyzed stereoselective formation of alpha-O-glycosides has been developed. This strategy relies on the palladium-biaryl phosphine catalyst-glycal donor complexation to control the anomeric selectivity. It does not depend on the nature of the protecting groups on the substrates, thus eliminating the need for cumbersome protecting group manipulations.

  DOI：

  10.1021/ol071268z

文献信息

• Palladium-Catalyzed Stereoselective Formation of α-<i>O</i>-Glycosides
  作者：Brandon P. Schuff、Gregory J. Mercer、Hien M. Nguyen

  DOI：10.1021/ol071268z

  日期：2007.8.1

  [GRAPHICS]A novel method for palladium-catalyzed stereoselective formation of alpha-O-glycosides has been developed. This strategy relies on the palladium-biaryl phosphine catalyst-glycal donor complexation to control the anomeric selectivity. It does not depend on the nature of the protecting groups on the substrates, thus eliminating the need for cumbersome protecting group manipulations.