ethyl 4,6-O-benzylidene-3-O-(p-chlorobenzyl)-1-thio-β-D-glucopyranoside | 1007885-88-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4,6-O-benzylidene-3-O-(p-chlorobenzyl)-1-thio-β-D-glucopyranoside
• 英文别名: (2R,4aR,6S,7R,8R,8aR)-8-[(4-chlorophenyl)methoxy]-6-ethylsulfanyl-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-ol
• CAS: 1007885-88-2
• 化学式: C₂₂H₂₅ClO₅S
• 分子量: 436.957
• InChiKey: CKOHCJSJSJVZQG-ILHTXMRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 4,6-O-benzylidene-3-O-(p-chlorobenzyl)-1-thio-β-D-glucopyranoside 、 4-碘苄基溴 在 四丁基碘化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以96%的产率得到ethyl 4,6-O-benzylidene-3-O-(p-chlorobenzyl)-2-O-(p-iodobenzyl)-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
• 作为产物：
  描述：

  、 苯甲醛二甲缩醛 在 camphor-10-sulfonic acid 作用下， 以 氯仿 为溶剂， 以13.80 g的产率得到ethyl 4,6-O-benzylidene-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

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.