p-tolyl 2,3-di-O-benzyl-5-O-(tert-butyldiphenylsilyl)-1-thio-α-D-arabinofuranoside | 917590-91-1

• 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-butyldiphenylsilyl)-1-thio-α-D-arabinofuranoside
• 英文别名: p-tolyl 2,3-di-O-benzyl-5-O-t-butyldiphenylsilyl-1-thio-α-D-arabinofuranoside
• CAS: 917590-91-1
• 化学式: C₄₂H₄₆O₄SSi
• 分子量: 674.976
• InChiKey: OHWSUALBUCBSPD-PRURZLHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.56
• 重原子数：
  48.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  p-tolyl 2,3-di-O-benzyl-5-O-(tert-butyldiphenylsilyl)-1-thio-α-D-arabinofuranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 四丁基氟化铵 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 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-2,3-di-O-acetyl-1-thio-α-D-arabinofuranoside 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.25h， 生成 p-tolyl 2,3-di-O-benzyl-5-O-(tert-butyldiphenylsilyl)-1-thio-α-D-arabinofuranoside
  参考文献：
  名称：

  Stereoselective Synthesis of a Fragment of Mycobacterial Arabinan

  摘要：

  Strategies for the stereoselective synthesis of mycobacterial arabinan were explored. Arabinofuranosyl donors with various protective groups were screened in terms of suitability for beta-( 1,2- cis)- selective glycosylation. The protective group was found to affect the stereoselectivity of arabinofuranosylation. beta-Selectivity was drastically enhanced by using donors protected with 3,5- TIDPS, possibly due to conformational constraints on the furanose ring. Synthesis of heptaarabinofuranoside was then performed to demonstrate the practicality of this methodology.

  DOI：

  10.1021/ol062198j

文献信息

• Neighboring-Group Participation by C-2 Ether Functions in Glycosylations Directed by Nitrile Solvents
  作者：Chin-Sheng Chao、Ching-Yu Lin、Shaheen Mulani、Wei-Cheng Hung、Kwok-kong Tony Mong

  DOI：10.1002/chem.201100732

  日期：2011.10.17

  Ether‐protecting functions at C‐2 hydroxy groups have been found to play participating roles in glycosylations when the reactions are conducted in nitrile solvent mixtures. The participation mechanism is based on intramolecular interaction between the lone electron pair of the oxygen atom of the C‐2 ether function and the nitrile molecule when they are positioned in a cis configuration. A 1,2‐cis glycosyl

  当在腈溶剂混合物中进行反应时，已发现在C-2羟基处的醚保护功能在糖基化中起参与作用。参与机制基于C-2醚功能的氧原子的孤电子对和腈分子以顺式排列时的分子内相互作用。形成一个1,2-顺式糖基恶唑啉鎓中间体。这种参与，再加上糖基供体的异头作用，赋予糖基化较高的1,2-反式选择性。该概念的进一步应用导致了α-（1→5）-阿拉伯低聚物的高效制备。
• β-Selective xylulofuranosylation <i>via</i> a conformationally-restricted glycosyl donor
  作者：Bo-Shun Huang、Todd L. Lowary

  DOI：10.1039/d0ob00260g

  日期：——

  Reported is the first stereoselective method for β-xylulofuranosylation, which employs 3,4-O-xylylene-protected thioglycoside donors.

  报道了第一种β-木糖呋喃糖基选择性方法，该方法使用3,4-O-二甲苯基保护的硫代糖苷供体。