N-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl)-1-(4-chlorophenyl)-3-phenylprop-2-ynylamine | 1164140-13-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: N-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl)-1-(4-chlorophenyl)-3-phenylprop-2-ynylamine
• 英文别名: [(2R,3R,4S,5R,6R)-6-[[(1R)-1-(4-chlorophenyl)-3-phenylprop-2-ynyl]amino]-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 1164140-13-9
• 化学式: C₄₁H₅₄ClNO₉
• 分子量: 740.334
• InChiKey: GKGREDFYQGOFKF-PGKJZTCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  52
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  苯乙炔 、 4-chloro-N-(2,3,4,6-tetra-O-pivaloyl-D-glucopyranosyl)benzylideneamine 在 copper(I) trifluoromethanesulfonate benzene 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 以92%的产率得到N-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl)-1-(4-chlorophenyl)-3-phenylprop-2-ynylamine
  参考文献：
  名称：

  Diastereoselective alkynylation of glucose-modified imines with terminal alkynes

  摘要：

  The copper(I)-catalyzed enantioselective alkynylation of aldimines incorporating a 2,3,4,6-tetrakis-O-pivaloyl-D-glucopyranosyl (Piv(4)Glc) chiral auxiliary with terminal alkynes is reported. The present system provides a versatile tool for the construction of optically active propargylamine derivatives Good. yields and enantiomeric excess values were achieved with an array of imines and biologically active, propargylamine derivatives. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.056

文献信息

• Diastereoselective alkynylation of glucose-modified imines with terminal alkynes
  作者：Jiangang Mao、Pengfei Zhang

  DOI：10.1016/j.tetasy.2009.02.056

  日期：2009.3

  The copper(I)-catalyzed enantioselective alkynylation of aldimines incorporating a 2,3,4,6-tetrakis-O-pivaloyl-D-glucopyranosyl (Piv(4)Glc) chiral auxiliary with terminal alkynes is reported. The present system provides a versatile tool for the construction of optically active propargylamine derivatives Good. yields and enantiomeric excess values were achieved with an array of imines and biologically active, propargylamine derivatives. (C) 2009 Elsevier Ltd. All rights reserved.