p-tolyl 2-O-acetyl-3-O-benzyl-5-O-tert-butydimethylsilyl-1-thio-α-D-arabinofuranoside | 1541168-26-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 2-O-acetyl-3-O-benzyl-5-O-tert-butydimethylsilyl-1-thio-α-D-arabinofuranoside
• CAS: 1541168-26-6
• 化学式: C₂₇H₃₈O₅SSi
• 分子量: 502.747
• InChiKey: WNRGLZBWDBYUHA-FXSWLTOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.35
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  p-tolyl 2-O-acetyl-3-O-benzyl-5-O-tert-butydimethylsilyl-1-thio-α-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 四丁基氟化铵 、 silver trifluoromethanesulfonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 3-azidopropyl-2-O-acetyl-3-O-benzyl-5-O-tert-butydimethylsilyl-α-D-arabinofuranosyl-(1→5)-2-O-acetyl-3-O-benzyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Synthetic and Immunological Studies of Mycobacterial Lipoarabinomannan Oligosaccharides and Their Protein Conjugates

  摘要：

  Lipoarabinomannan (LAM) is one of the major constituents of the Mycobacterium tuberculosis cell wall and an attractive molecular scaffold for antituberculosis drug and vaccine development. In this paper, a convergent strategy was developed for the synthesis of LAM oligosaccharides with an alpha-1,2-linked dimannopyranose cap at the nonreducing end. The strategy was highlighted by efficient coupling of separately prepared nonreducing end and reducing end oligosaccharides. Glycosylations were mainly achieved with thioglycoside donors, which gave excellent yields and stereoselectivity even for reactions between complex oligosaccharides. The strategy was utilized to successfully synthesize tetra-, hepta-, and undecasaccharides of LAM from D-arabinose in 10, 15, and 14 longest linear steps and 7.84, 7.50, and 2.59% overall yields, respectively. The resultant oligosaccharides with a free amino group at their reducing end were effectively conjugated with carrier proteins, including bovine serum albumin and keyhole limpet hemocyanin (KLH), via a bifunctional linker. Preliminary immunological studies on the KLH conjugates revealed that they could elicit robust antibody responses in mice and that the antigen structure had some influence on their immunological property, thus verifying the potential of the oligosaccharides for vaccine development and other immunological studies.

  DOI：

  10.1021/acs.joc.5b01686
• 作为产物：
  描述：

  在 吡啶 、 4-二甲氨基吡啶 、 四氯化锡 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 2.5h， 生成 p-tolyl 2-O-acetyl-3-O-benzyl-5-O-tert-butydimethylsilyl-1-thio-α-D-arabinofuranoside
  参考文献：
  名称：

  一种微型脂阿拉伯甘露聚糖的合成

  摘要：

  已经合成了结核分枝杆菌脂阿拉伯甘露聚糖 (LAM)的类似物，包含其所有三个主要成分的特征结构；即，甘露糖化的磷脂酰肌醇部分、低聚甘露聚糖和低聚阿拉伯聚糖。开发了一种高度收敛的策略，适用于其他 LAM 类似物的合成。合成微型 LAM 应可用于各种生物学研究。

  DOI：

  10.1021/ol4036903