Benzoic acid (2R,3R,4S,5R)-3,4-bis-benzyloxy-5-p-tolylsulfanyl-tetrahydro-furan-2-ylmethyl ester | 367274-92-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzoic acid (2R,3R,4S,5R)-3,4-bis-benzyloxy-5-p-tolylsulfanyl-tetrahydro-furan-2-ylmethyl ester
• 英文别名: [(2R,3R,4S,5R)-5-(4-methylphenyl)sulfanyl-3,4-bis(phenylmethoxy)oxolan-2-yl]methyl benzoate
• CAS: 367274-92-8
• 化学式: C₃₃H₃₂O₅S
• 分子量: 540.68
• InChiKey: HOGZMXZJHGBJOT-RASQHNTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  79.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside 、 Benzoic acid (2R,3R,4S,5R)-3,4-bis-benzyloxy-5-p-tolylsulfanyl-tetrahydro-furan-2-ylmethyl ester 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 生成 、
  参考文献：
  名称：

  Synthesis of arabinofuranosides via low-temperature activation of thioglycosides

  摘要：

  The synthesis of oligosaccharides containing arabinofuranose residues is reported. Coupling of thioglycoside donors 4, 6, or 7 and with acceptors 8-17 using N-iodosuccinimide and silver triflate activation provided glycosides with varying degrees of stereocontrol. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01133-9
• 作为产物：
  描述：

  p-tolyl 5-O-t-butyldiphenylsilyl-1-thio-α-D-arabinofuranoside 在 吡啶 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 Benzoic acid (2R,3R,4S,5R)-3,4-bis-benzyloxy-5-p-tolylsulfanyl-tetrahydro-furan-2-ylmethyl ester
  参考文献：
  名称：

  Synthesis of arabinofuranosides via low-temperature activation of thioglycosides

  摘要：

  The synthesis of oligosaccharides containing arabinofuranose residues is reported. Coupling of thioglycoside donors 4, 6, or 7 and with acceptors 8-17 using N-iodosuccinimide and silver triflate activation provided glycosides with varying degrees of stereocontrol. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01133-9

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.
• Synthesis of arabinofuranosides via low-temperature activation of thioglycosides
  作者：Haifeng Yin、Todd L Lowary

  DOI：10.1016/s0040-4039(01)01133-9

  日期：2001.8

  The synthesis of oligosaccharides containing arabinofuranose residues is reported. Coupling of thioglycoside donors 4, 6, or 7 and with acceptors 8-17 using N-iodosuccinimide and silver triflate activation provided glycosides with varying degrees of stereocontrol. (C) 2001 Elsevier Science Ltd. All rights reserved.