1,3,4,6-tetra-O-acetyl-2-deoxy-2-({[2-(diphenylphosphino)phenyl]acetyl}amino)-β-D-glucopyranose | 870193-17-2

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-({[2-(diphenylphosphino)phenyl]acetyl}amino)-β-D-glucopyranose
• 英文别名: [(2R,3S,4R,5R,6S)-3,4,6-triacetyloxy-5-[[2-(2-diphenylphosphanylphenyl)acetyl]amino]oxan-2-yl]methyl acetate
• CAS: 870193-17-2
• 化学式: C₃₄H₃₆NO₁₀P
• 分子量: 649.634
• InChiKey: SNMJTZWIEVHISM-BNNJPYFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  144
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-({[2-(diphenylphosphino)phenyl]acetyl}amino)-β-D-glucopyranose 在 三乙烯二胺 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 96.0h， 生成 1,3,4,6-tetra-O-acetyl-2-deoxy-2-{[(3R)-3-(diphenylphosphino)pentanoyl]amino}-β-D-glucopyranose
  参考文献：
  名称：

  Influence on the enantioselectivity in allylic alkylation of the spacer between the amido group of d-glucosamine and the diphenylphosphino group

  摘要：

  The synthesis of a new generation of chiral phosphine-amides derived from D-glucosamine is described. The palladium-catalyzed asymmetric allylic alkylation of racemic 1,3-diphenyl-2-propenyl acetate with dimethyl malonate has been investigated. The results obtained from these new ligands showed the importance of the rigidity of the complex and of the D-glucosamine skeleton on the enantioselectivity of the reaction. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.035
• 作为产物：
  描述：

  2-[2-(diphenylphosphino)phenyl]acetic acid 、 tetra-acetyl glucosamine 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.0h， 以62%的产率得到1,3,4,6-tetra-O-acetyl-2-deoxy-2-({[2-(diphenylphosphino)phenyl]acetyl}amino)-β-D-glucopyranose
  参考文献：
  名称：

  Influence on the enantioselectivity in allylic alkylation of the spacer between the amido group of d-glucosamine and the diphenylphosphino group

  摘要：

  The synthesis of a new generation of chiral phosphine-amides derived from D-glucosamine is described. The palladium-catalyzed asymmetric allylic alkylation of racemic 1,3-diphenyl-2-propenyl acetate with dimethyl malonate has been investigated. The results obtained from these new ligands showed the importance of the rigidity of the complex and of the D-glucosamine skeleton on the enantioselectivity of the reaction. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.035