p-tolyl-2,3-di-O-benzyl-5-O-tert-butydimethylsilyl-1-thio-α-D-arabinofuranoside | 1236193-27-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl-2,3-di-O-benzyl-5-O-tert-butydimethylsilyl-1-thio-α-D-arabinofuranoside
• 英文别名: p-tolyl 2,3-di-O-benzyl-5-O-tert-butyldimethylsilyl-1-thio-α-D-arabinofuranoside；tert-butyl-dimethyl-[[(2R,3R,4S,5R)-5-(4-methylphenyl)sulfanyl-3,4-bis(phenylmethoxy)oxolan-2-yl]methoxy]silane
• CAS: 1236193-27-3
• 化学式: C₃₂H₄₂O₄SSi
• 分子量: 550.835
• InChiKey: NJUUPCGYQQAAEQ-LTXXGDHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.0
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  p-tolyl-2,3-di-O-benzyl-5-O-tert-butydimethylsilyl-1-thio-α-D-arabinofuranoside 在 N-溴代丁二酰亚胺(NBS) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 5.0h， 生成 2,3-O-benzyl-5-O-TBS-D-arabinofuranosyltrichloroacetimidate
  参考文献：
  名称：

  10.1016/j.carres.2024.109204

  摘要：

  DOI：

  10.1016/j.carres.2024.109204
• 作为产物：
  描述：

  4-甲苯硫酚 在 sodium methylate 、 四氯化锡 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.67h， 生成 p-tolyl-2,3-di-O-benzyl-5-O-tert-butydimethylsilyl-1-thio-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

文献信息

• Probing the Effect of Acylation on Arabinofuranose Ring Conformation in Di- and Trisaccharide Fragments of Mycobacterial Arabinogalactan
  作者：Chunjuan Liu、Michele R. Richards、Todd L. Lowary

  DOI：10.1021/jo100575a

  日期：2010.8.6

  A major component of the cell wall of mycobacteria is the mycolyl-arabinogalactan (mAG) complex. The arabinose and galactose residues in mAG are found solely in the furanose form, and it has been suggested that the flexibility of these five-membered rings allows for the tight packing of mycolic acids. In order to probe the "flexible scaffold hypothesis", we designed and synthesized glycolipids 3-6 and 8-11 as simple models of the terminal portion of mAG. A set of donors and acceptors were explored for preparing the key beta-(1 -> 2) linkage in 2-6, and the best selectivity and yield can be obtained by using the electron-rich thioglycoside donor 14 and the O-5 p-methoxybenzyl-protected acceptor 17. Both alpha-linkages in the trisaccharides 7-11 were formed in a one-pot reaction. The conformations of compounds 2-11 were studied using solution-state NMR spectroscopy, but little change was observed in the coupling constants for the ring protons between 2 and 3-6 or between 7 and 8-11. However, the rotamer populations about the C-4-C-5 bond for the beta-linked ring in disaccharide 2 did change upon acylation at O-5.
• 10.1016/j.carres.2024.109204
  作者：Fang, Sixian、Huang, Cai、Ao, Jiaming、Xiao, Qian、Zhou, Siai、Deng, Wenbin、Cai, Hui、Ding, Feiqing

  DOI：10.1016/j.carres.2024.109204

  日期：——
• Synthetic and Immunological Studies of Mycobacterial Lipoarabinomannan Oligosaccharides and Their Protein Conjugates
  作者：Lizhen Wang、Shaojie Feng、Lian An、Guofeng Gu、Zhongwu Guo

  DOI：10.1021/acs.joc.5b01686

  日期：2015.10.16

  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.