3-O-(p-chlorobenzyl)-β-D-glucopyranose | 1007885-85-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-(p-chlorobenzyl)-β-D-glucopyranose
• 英文别名: (2R,3R,4S,5R,6R)-4-[(4-chlorophenyl)methoxy]-6-(hydroxymethyl)oxane-2,3,5-triol
• CAS: 1007885-85-9
• 化学式: C₁₃H₁₇ClO₆
• 分子量: 304.727
• InChiKey: MRUNICVDDNUTIF-NJMOYASZSA-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：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-O-(p-chlorobenzyl)-β-D-glucopyranose 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 生成 1,2,4,6-tetra-O-acetyl-3-O-(p-chlorobenzyl)-β-D-glucopyranose 、 1,2,4,6-tetra-O-acetyl-3-O-(p-chlorobenzyl)-α-D-glucopyranose
  参考文献：
  名称：

  Synthetic Studies toward Mycobacterium tuberculosis Sulfolipid-I

  摘要：

  [GRAPHICS]Sulfolipid-I (SL-I) is an abundant metabolite found in the cell wall of Mycobacterium tuberculosis that is comprised of a trehalose 2-sulfate core modified with four fatty acyl substituents. The correlation of its abundance with the virulence of clinical isolates suggests a role for SL-I in pathogenesis, although its biological functions remain unknown. Here we describe the synthesis of a SL-I analogue bearing unnatural lipid substituents. A key feature of the synthesis was application of an intramolecular aglycon delivery reaction to join two differentially protected glucose monomers, one prepared with a novel alpha-selective glycosylation. The route developed for the model compound can be readily extended to the synthesis of native SL-I as well as additional analogues for use in the investigation of SL-I's functions.

  DOI：

  10.1021/jo702032c
• 作为产物：
  描述：

  3-O-(p-chlorobenzyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 Dowex 50WX₈-400 resin H+ 作用下， 以 水 为溶剂， 以93%的产率得到3-O-(p-chlorobenzyl)-β-D-glucopyranose
  参考文献：
  名称：

  Synthetic Studies toward Mycobacterium tuberculosis Sulfolipid-I

  摘要：

  [GRAPHICS]Sulfolipid-I (SL-I) is an abundant metabolite found in the cell wall of Mycobacterium tuberculosis that is comprised of a trehalose 2-sulfate core modified with four fatty acyl substituents. The correlation of its abundance with the virulence of clinical isolates suggests a role for SL-I in pathogenesis, although its biological functions remain unknown. Here we describe the synthesis of a SL-I analogue bearing unnatural lipid substituents. A key feature of the synthesis was application of an intramolecular aglycon delivery reaction to join two differentially protected glucose monomers, one prepared with a novel alpha-selective glycosylation. The route developed for the model compound can be readily extended to the synthesis of native SL-I as well as additional analogues for use in the investigation of SL-I's functions.

  DOI：

  10.1021/jo702032c

文献信息

• Synthetic Studies toward <i>Mycobacterium tuberculosis</i> Sulfolipid-I
  作者：Clifton D. Leigh、Carolyn R. Bertozzi

  DOI：10.1021/jo702032c

  日期：2008.2.1

  [GRAPHICS]Sulfolipid-I (SL-I) is an abundant metabolite found in the cell wall of Mycobacterium tuberculosis that is comprised of a trehalose 2-sulfate core modified with four fatty acyl substituents. The correlation of its abundance with the virulence of clinical isolates suggests a role for SL-I in pathogenesis, although its biological functions remain unknown. Here we describe the synthesis of a SL-I analogue bearing unnatural lipid substituents. A key feature of the synthesis was application of an intramolecular aglycon delivery reaction to join two differentially protected glucose monomers, one prepared with a novel alpha-selective glycosylation. The route developed for the model compound can be readily extended to the synthesis of native SL-I as well as additional analogues for use in the investigation of SL-I's functions.