pentachlorophenyl 6-azido-6-deoxy-2,3,4,5-tetra-O-methyl-L-galactonate | 848442-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: pentachlorophenyl 6-azido-6-deoxy-2,3,4,5-tetra-O-methyl-L-galactonate
• 英文别名: (2,3,4,5,6-pentachlorophenyl) (2S,3R,4R,5S)-6-azido-2,3,4,5-tetramethoxyhexanoate
• CAS: 848442-36-4
• 化学式: C₁₆H₁₈Cl₅N₃O₆
• 分子量: 525.6
• InChiKey: PPLFUTKARMDYAO-JYWGMUSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  77.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  pentachlorophenyl 6-azido-6-deoxy-2,3,4,5-tetra-O-methyl-L-galactonate 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、310.26 kPa 条件下， 反应 26.0h， 生成 6-(6'-(tert-butoxycarbonylamino)-6'-deoxy-2',3',4',5'-tetra-O-methyl-L-galactonamido)-6-deoxy-2,3,4,5-tetra-O-methyl-L-galactonic acid
  参考文献：
  名称：

  Synthesis of stereoregular poly-O-methyl-d- and l-polygalactonamides as nylon 6 analogues

  摘要：

  Conveniently activated dimers: (pentachlorophenyl 6-(6'-(tert-butoxycarbonylamino)-6'-deoxy-2',3',4',5',-tetra-O-methyl-D-galactonamide)-6'-deoxy-2,3,4,5-tetra-O-methyl-D-galactonate) 7 and its analogue in the L-series 16. were prepared: respectively, from 6-amino-6-deoxy-D- and L-galactonic acid derivatives 5 and 14. Upon release of the amino function of 7 under acidic conditions, polymerization was conducted in a non-polar (CHCl3) or a polar solvent (DMF) affording poly(6-amino-6-deoxy-2,3,4,5-tetra-O-methyl-D-galactonic acid) 11. Similarly, polymerization in DMF from 16 gave the polygalactonamide 18 (L-series). The polyamides were characterized by IR and NMR spectroscopies. The latter technique was also employed for establishing the conformation of 11 in CDCl3 solution. Molecular weights (about 11,000) were estimated by viscosimetry and size exclusion chromatography. Polygalactonamides 11 and 18 were highly hygroscopic and soluble in a variety, of organic solvents. including chloroform. The thermal behavior of the polyamides was also studied. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.061
• 作为产物：
  描述：

  五氯酚 、 6-azido-6-deoxy-2,3,4,5-tetra-O-methyl-L-galactonic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 以88%的产率得到pentachlorophenyl 6-azido-6-deoxy-2,3,4,5-tetra-O-methyl-L-galactonate
  参考文献：
  名称：

  Synthesis of stereoregular poly-O-methyl-d- and l-polygalactonamides as nylon 6 analogues

  摘要：

  Conveniently activated dimers: (pentachlorophenyl 6-(6'-(tert-butoxycarbonylamino)-6'-deoxy-2',3',4',5',-tetra-O-methyl-D-galactonamide)-6'-deoxy-2,3,4,5-tetra-O-methyl-D-galactonate) 7 and its analogue in the L-series 16. were prepared: respectively, from 6-amino-6-deoxy-D- and L-galactonic acid derivatives 5 and 14. Upon release of the amino function of 7 under acidic conditions, polymerization was conducted in a non-polar (CHCl3) or a polar solvent (DMF) affording poly(6-amino-6-deoxy-2,3,4,5-tetra-O-methyl-D-galactonic acid) 11. Similarly, polymerization in DMF from 16 gave the polygalactonamide 18 (L-series). The polyamides were characterized by IR and NMR spectroscopies. The latter technique was also employed for establishing the conformation of 11 in CDCl3 solution. Molecular weights (about 11,000) were estimated by viscosimetry and size exclusion chromatography. Polygalactonamides 11 and 18 were highly hygroscopic and soluble in a variety, of organic solvents. including chloroform. The thermal behavior of the polyamides was also studied. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.061

文献信息

• Synthesis of stereoregular poly-O-methyl-d- and l-polygalactonamides as nylon 6 analogues
  作者：Carmen L. Romero Zaliz、Oscar Varela

  DOI：10.1016/j.tetasy.2004.11.061

  日期：2005.1

  Conveniently activated dimers: (pentachlorophenyl 6-(6'-(tert-butoxycarbonylamino)-6'-deoxy-2',3',4',5',-tetra-O-methyl-D-galactonamide)-6'-deoxy-2,3,4,5-tetra-O-methyl-D-galactonate) 7 and its analogue in the L-series 16. were prepared: respectively, from 6-amino-6-deoxy-D- and L-galactonic acid derivatives 5 and 14. Upon release of the amino function of 7 under acidic conditions, polymerization was conducted in a non-polar (CHCl3) or a polar solvent (DMF) affording poly(6-amino-6-deoxy-2,3,4,5-tetra-O-methyl-D-galactonic acid) 11. Similarly, polymerization in DMF from 16 gave the polygalactonamide 18 (L-series). The polyamides were characterized by IR and NMR spectroscopies. The latter technique was also employed for establishing the conformation of 11 in CDCl3 solution. Molecular weights (about 11,000) were estimated by viscosimetry and size exclusion chromatography. Polygalactonamides 11 and 18 were highly hygroscopic and soluble in a variety, of organic solvents. including chloroform. The thermal behavior of the polyamides was also studied. (C) 2004 Elsevier Ltd. All rights reserved.