6-amino-6-deoxy-2,3,4,5-tetra-O-methyl-L-galactonic acid | 620609-72-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-amino-6-deoxy-2,3,4,5-tetra-O-methyl-L-galactonic acid
• 英文别名: (2S,3R,4R,5S)-6-amino-2,3,4,5-tetramethoxyhexanoic acid
• CAS: 620609-72-5
• 化学式: C₁₀H₂₁NO₆
• 分子量: 251.28
• InChiKey: MLHIMAZSUVUBOK-KDXUFGMBSA-N

物化性质

• 熔点：
  172 °C (decomp)
• 沸点：
  372.3±42.0 °C(Predicted)
• 密度：
  1.148±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  7

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 、 6-amino-6-deoxy-2,3,4,5-tetra-O-methyl-L-galactonic acid 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以76%的产率得到6-(6'-azido-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：

  6-azido-6-deoxy-2,3,4,5-tetra-O-methyl-L-galactonic acid 在 钯 氢气 作用下， 以93%的产率得到6-amino-6-deoxy-2,3,4,5-tetra-O-methyl-L-galactonic acid
  参考文献：
  名称：

  Straightforward synthesis of derivatives of d- and l-galactonic acids as precursors of stereoregular polymers

  摘要：

  High yielding routes for the synthesis of selectively protected derivatives Of D- and L-galactonic acids. having free OH or NH2 groups at the C-6 position, are reported. The successful direct per-O-methylation of galactonic acid derivatives from the corresponding galactono- 1.4-lactones was developed as a key step of the sequence. For example. 6-azido-6-deoxy-L-galactono- 1.4-lactone 16 was converted into the potassium salt and methylated (NaH, DMSO, Mel) to the methyl ester of the 2,3.4,5-tetra-O-methyl derivative 12. Compound 16 was readily prepared by bromination at C-6 Of L-galactonolactone 1 and isopropylidenation followed by substitution of bromine by azide and removal of the protecting groups. Hydrolysis of the methyl ester of 12 and hydrogenation of the azide led to the tetra-O-methyl derivative of the 6-amino acid 18 with 52% overall yield from 1. The same sequence applied to D-galactonolactone 19 led to the enantiomeric amino acid 25 with a 47% overall yield. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00588-3

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.
• Straightforward synthesis of derivatives of d- and l-galactonic acids as precursors of stereoregular polymers
  作者：Carmen L. Romero Zaliz、Oscar Varela

  DOI：10.1016/s0957-4166(03)00588-3

  日期：2003.9

  High yielding routes for the synthesis of selectively protected derivatives Of D- and L-galactonic acids. having free OH or NH2 groups at the C-6 position, are reported. The successful direct per-O-methylation of galactonic acid derivatives from the corresponding galactono- 1.4-lactones was developed as a key step of the sequence. For example. 6-azido-6-deoxy-L-galactono- 1.4-lactone 16 was converted into the potassium salt and methylated (NaH, DMSO, Mel) to the methyl ester of the 2,3.4,5-tetra-O-methyl derivative 12. Compound 16 was readily prepared by bromination at C-6 Of L-galactonolactone 1 and isopropylidenation followed by substitution of bromine by azide and removal of the protecting groups. Hydrolysis of the methyl ester of 12 and hydrogenation of the azide led to the tetra-O-methyl derivative of the 6-amino acid 18 with 52% overall yield from 1. The same sequence applied to D-galactonolactone 19 led to the enantiomeric amino acid 25 with a 47% overall yield. (C) 2003 Elsevier Ltd. All rights reserved.