p-tolyl 3,5-O-(di-tert-butylsilylene)-1-thio-2-O-triisopropylsilyl-α-D-arabinofuranoside | 917590-99-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚酯
• 英文名称: p-tolyl 3,5-O-(di-tert-butylsilylene)-1-thio-2-O-triisopropylsilyl-α-D-arabinofuranoside
• CAS: 917590-99-9
• 化学式: C₂₉H₅₂O₄SSi₂
• 分子量: 552.966
• InChiKey: RZCOFMCLLVQPAU-JVYGEBFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.83
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  benzyl 3,5-di-O-benzyl-α-D-arabinofuranoside 、 p-tolyl 3,5-O-(di-tert-butylsilylene)-1-thio-2-O-triisopropylsilyl-α-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 3 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 benzyl 3,5-O-(di-tert-butylsilylene)-2-O-triisopropylsilyl-β-D-arabinofuranosyl-(1->2)-3,5-O-dibenzyl-α-D-arabinofuranoside 、 benzyl 3,5-O-(di-tert-butylsilylene)-2-O-triisopropylsilyl-α-D-arabinofuranosyl-(1->2)-3,5-O-dibenzyl-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
• 作为产物：
  描述：

  1,2,3-tri-O-acetyl-5-O-t-butyldiphenylsilyl-D-arabinofuranose 在 咪唑 、 2,6-二甲基吡啶 、 三氟化硼乙醚 、 四丁基氟化铵 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.75h， 生成 p-tolyl 3,5-O-(di-tert-butylsilylene)-1-thio-2-O-triisopropylsilyl-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