methyl 3,6-anhydro-2,4,5-tri-O-methyl-L-galactonate | 18427-27-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: methyl 3,6-anhydro-2,4,5-tri-O-methyl-L-galactonate
• 英文别名: 2,4,5-Tri-O-methyl-3,6-anhydro-L-galactonsaeuremethylester；tri-O-methyl-3,6-anhydro-L-galactonic acid methyl ester；Tri-O-methyl-3,6-anhydro-L-galactonsaeure-methylester；methyl (2S)-2-[(2R,3R,4S)-3,4-dimethoxyoxolan-2-yl]-2-methoxyacetate
• CAS: 18427-27-5
• 化学式: C₁₀H₁₈O₆
• 分子量: 234.249
• InChiKey: JJTZSAUMDJMGHX-KDXUFGMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methyl 2,3,4,5-tetra-O-methyl-6-O-tosyl-L-galactonate 以 甲苯 为溶剂， 反应 16.0h， 以92%的产率得到methyl 3,6-anhydro-2,4,5-tri-O-methyl-L-galactonate
  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

• Araki, Nippon Kagaku Kaishi/Journal of the Chemical Society of Japan, 1944, vol. 65, p. 627,630
  作者：Araki

  DOI：——

  日期：——
• Araki, Nippon Kagaku Kaishi/Journal of the Chemical Society of Japan, 1940, vol. 61, p. 775,779
  作者：Araki

  DOI：——

  日期：——
• 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.