methyl 5,6-O-isopropylidene-2,3,4-tri-O-methyl-L-galactonate | 620609-60-1

• 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: methyl 5,6-O-isopropylidene-2,3,4-tri-O-methyl-L-galactonate
• 英文别名: methyl (2S,3R,4R)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,3,4-trimethoxybutanoate
• CAS: 620609-60-1
• 化学式: C₁₃H₂₄O₇
• 分子量: 292.329
• InChiKey: SLCOUACIXGSOIS-ZDCRXTMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 5,6-O-isopropylidene-2,3,4-tri-O-methyl-L-galactonate 在 盐酸 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (3S,4R,5R,6S)-6-Azidomethyl-3,4,5-trimethoxy-tetrahydro-pyran-2-one
  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
• 作为产物：
  描述：

  5,6-O-isopropylidene-L-galactonic acid γ-lactone 、 碘甲烷 在 氢氧化钾 、 sodium hydride 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 2.0h， 以56%的产率得到methyl 5,6-O-isopropylidene-2,3,4-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

• 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.