N-[(2R,4aR,6S,7R,8R,8aS)-8-hydroxy-2-(4-methoxyphenyl)-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-2-diphenylphosphanylbenzamide | 1225431-73-1

• 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: N-[(2R,4aR,6S,7R,8R,8aS)-8-hydroxy-2-(4-methoxyphenyl)-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-2-diphenylphosphanylbenzamide
• CAS: 1225431-73-1
• 化学式: C₄₀H₃₈NO₇P
• 分子量: 675.718
• InChiKey: YJLWQQTWYYMYOO-SNLZTSHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  49
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  95.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[(2R,4aR,6S,7R,8R,8aS)-8-hydroxy-2-(4-methoxyphenyl)-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-2-diphenylphosphanylbenzamide 、 2,2-二苯基丙酸 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 12.0h， 生成 [(2R,4aR,6S,7R,8R,8aS)-7-[(2-diphenylphosphanylbenzoyl)amino]-2-(4-methoxyphenyl)-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 2,2-diphenylpropanoate
  参考文献：
  名称：

  Naplephos: a modular library of chiral phosphines based on d-glucose for highly enantioselective asymmetric catalysis

  摘要：

  Simple functionalisation of N-acetylglucosamine produces the modular ligand library naplephos, which combines the performance of 'privileged' ligands based on 1,2-trans-cyclohexanediamine with flexibility and accessibility. With the proper choice of substituents, the basic structure was suitably adapted to the Pd-catalysed asymmetric allylic alkylation of rac-(E)-1,3-dipheny1-2-propenyl acetate with dimethyl malonate, producing the (S)-product in ee's of up to 96% ee. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.01.005
• 作为产物：
  描述：

  benzyl 2-amino-2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside 、 2-二苯基膦苯甲酸 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 12.0h， 以85%的产率得到N-[(2R,4aR,6S,7R,8R,8aS)-8-hydroxy-2-(4-methoxyphenyl)-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-2-diphenylphosphanylbenzamide
  参考文献：
  名称：

  Naplephos: a modular library of chiral phosphines based on d-glucose for highly enantioselective asymmetric catalysis

  摘要：

  Simple functionalisation of N-acetylglucosamine produces the modular ligand library naplephos, which combines the performance of 'privileged' ligands based on 1,2-trans-cyclohexanediamine with flexibility and accessibility. With the proper choice of substituents, the basic structure was suitably adapted to the Pd-catalysed asymmetric allylic alkylation of rac-(E)-1,3-dipheny1-2-propenyl acetate with dimethyl malonate, producing the (S)-product in ee's of up to 96% ee. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.01.005

文献信息

• Naplephos: a modular library of chiral phosphines based on d-glucose for highly enantioselective asymmetric catalysis
  作者：Vincenzo Benessere、Francesco Ruffo

  DOI：10.1016/j.tetasy.2010.01.005

  日期：2010.2

  Simple functionalisation of N-acetylglucosamine produces the modular ligand library naplephos, which combines the performance of 'privileged' ligands based on 1,2-trans-cyclohexanediamine with flexibility and accessibility. With the proper choice of substituents, the basic structure was suitably adapted to the Pd-catalysed asymmetric allylic alkylation of rac-(E)-1,3-dipheny1-2-propenyl acetate with dimethyl malonate, producing the (S)-product in ee's of up to 96% ee. (C) 2010 Elsevier Ltd. All rights reserved.