[(2R,4aR,6S,7R,8S,8aR)-7-[4,8-bis(trimethylsilyl)benzo[d][1,3,2]benzodioxaphosphepin-6-yl]oxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] pyridine-2-carboxylate | 1395506-14-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: [(2R,4aR,6S,7R,8S,8aR)-7-[4,8-bis(trimethylsilyl)benzo[d][1,3,2]benzodioxaphosphepin-6-yl]oxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] pyridine-2-carboxylate
• CAS: 1395506-14-5
• 化学式: C₃₈H₄₄NO₉PSi₂
• 分子量: 745.913
• InChiKey: YVAPVBSVYSBIAD-HQFSDMCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.28
• 重原子数：
  51
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-3-O-picolinyl-α-D-glucopyranoside 、 6-Chloro-4,8-bis-trimethylsilanyl-5,7-dioxa-6-phospha-dibenzo[a,c]cycloheptene 在 吡啶 作用下， 以 甲苯 为溶剂， 生成 [(2R,4aR,6S,7R,8S,8aR)-7-[4,8-bis(trimethylsilyl)benzo[d][1,3,2]benzodioxaphosphepin-6-yl]oxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] pyridine-2-carboxylate
  参考文献：
  名称：

  吡喃糖苷亚磷酸酯-吡啶配体在对映选择性金属催化的烯丙基取代和共轭1,4-加成中的应用

  摘要：

  在金属催化的烯丙基取代和几种底物类型的共轭1，4-加成反应中已应用了一系列的吡喃葡萄糖苷亚磷酸酯-吡啶配体。我们已经能够鉴定出在环状底物的Pd催化的分子间烯丙基取代（ee高达86％）和去对称化（ee高达94％）以及铜催化的挑战性脂族烯酮的共轭加成中提供有希望的对映选择性的配体。 （ee高达90％）。

  DOI：

  10.1016/j.tetasy.2013.06.011

文献信息

• The application of pyranoside phosphite-pyridine ligands to enantioselective Ir-catalyzed hydrogenations of highly unfunctionalized olefins
  作者：Jessica Margalef、Matteo Lega、Francesco Ruffo、Oscar Pàmies、Montserrat Diéguez

  DOI：10.1016/j.tetasy.2012.06.025

  日期：2012.7

  Eight (biaryl)phosphite/pyridine ligands 1-2a-d have been prepared by the modular functionalization of positions C-2 and C-3 of two D-glucopyranoside backbones. The chiral ligands were examined in the iridium-catalyzed asymmetric hydrogenation of poorly functionalized alkenes, as a function of the relative position of the coordinating groups and the geometric properties of the biaryl phosphite moieties. Enantiomeric excesses of up to 90% were achieved in the hydrogenation of E-2-(4-methoxyphenyl)-2-butene by using 1a and 1c, which seemingly combine the beneficial effect of the phosphite at the 2-position with the matching (R-ax)-configuration of their encumbered biaryl substituents. The results of the hydrogenation of more challenging substrates, such as Z-trisubstituted alkenes, alkenes with a neighboring polar group or demanding 1,1-di-substituted alkenes, generally confirmed this trend, and in some significant cases, the chiral hydrogenated products were isolated with ees of 65-79%. (C) 2012 Elsevier Ltd. All rights reserved.