ethyl 2,4,6-tri-O-acetyl-3-O-(p-chlorobenzyl)-1-thio-β-D-glucopyranoside | 1007885-87-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,4,6-tri-O-acetyl-3-O-(p-chlorobenzyl)-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3,5-diacetyloxy-4-[(4-chlorophenyl)methoxy]-6-ethylsulfanyloxan-2-yl]methyl acetate
• CAS: 1007885-87-1
• 化学式: C₂₁H₂₇ClO₈S
• 分子量: 474.96
• InChiKey: GTQKUPZVLZAYGY-ADAARDCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 2,4,6-tri-O-acetyl-3-O-(p-chlorobenzyl)-1-thio-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成
  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：

  1,2,4,6-tetra-O-acetyl-3-O-(p-chlorobenzyl)-β-D-glucopyranose 、 乙硫醇 在 三氟化硼乙醚 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 144.0h， 以80%的产率得到ethyl 2,4,6-tri-O-acetyl-3-O-(p-chlorobenzyl)-1-thio-β-D-glucopyranoside
  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