(-)-1,2:5,6-di-O-isopropylidene-3,4-bis-O-<2'-(diphenylphosphino)benzoyl>-D-mannitol | 138517-60-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (-)-1,2:5,6-di-O-isopropylidene-3,4-bis-O-<2'-(diphenylphosphino)benzoyl>-D-mannitol
• 英文别名: [(1R,2R)-1,2-bis[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(2-diphenylphosphanylbenzoyl)oxyethyl] 2-diphenylphosphanylbenzoate
• CAS: 138517-60-9
• 化学式: C₅₀H₄₈O₈P₂
• 分子量: 838.874
• InChiKey: FDIMFOZCFKDOMM-KHJRNFQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  60
• 可旋转键数：
  15
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-二苯基膦苯甲酸 、 双丙酮-D-甘露糖醇 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 以13.2%的产率得到(-)-1,2:5,6-di-O-isopropylidene-3,4-bis-O-<2'-(diphenylphosphino)benzoyl>-D-mannitol
  参考文献：
  名称：

  A modular approach for ligand design for asymmetric allylic alkylations via enantioselective palladium-catalyzed ionizations

  摘要：

  A new class of ligands for asymmetric transition metal catalysis based on 2-(diphenylphosphino)benzoic acid was used in a mechanistically-defined palladium-catalyzed reaction in which enantiodifferentiation was the result of selective ionization of substrates derived from cis-2-cycloalkene-1,4-diols. By making rational, stepwise changes in the ligand structure, the structural requirements for good asymmetric induction were probed. The absolute stereochemistry of the products was found to be related to the chirality of the ligand in a predictable fashion. A mnemonic is given which allows one to predict the mode of ionization (R or S) solely on the basis of the stereochemistry of the variable chiral linker used to make the ligand.

  DOI：

  10.1021/ja00050a013

文献信息

• Trost, Barry M.; Vranken, David L. Van, Angewandte Chemie, 1992, vol. 104, # 2, p. 194 - 196
  作者：Trost, Barry M.、Vranken, David L. Van

  DOI：——

  日期：——
• US5739396A
  申请人：——

  公开号：US5739396A

  公开（公告）日：1998-04-14
• A modular approach for ligand design for asymmetric allylic alkylations via enantioselective palladium-catalyzed ionizations
  作者：Barry M. Trost、David L. Van Vranken、Carsten Bingel

  DOI：10.1021/ja00050a013

  日期：1992.11

  A new class of ligands for asymmetric transition metal catalysis based on 2-(diphenylphosphino)benzoic acid was used in a mechanistically-defined palladium-catalyzed reaction in which enantiodifferentiation was the result of selective ionization of substrates derived from cis-2-cycloalkene-1,4-diols. By making rational, stepwise changes in the ligand structure, the structural requirements for good asymmetric induction were probed. The absolute stereochemistry of the products was found to be related to the chirality of the ligand in a predictable fashion. A mnemonic is given which allows one to predict the mode of ionization (R or S) solely on the basis of the stereochemistry of the variable chiral linker used to make the ligand.