benzyl 2,3,5,6-tetra-O-tert-butyldimethylsilyl-1-thio-α-D-galactofuranoside | 1415315-82-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3,5,6-tetra-O-tert-butyldimethylsilyl-1-thio-α-D-galactofuranoside
• CAS: 1415315-82-0
• 化学式: C₃₇H₇₄O₅SSi₄
• 分子量: 743.4
• InChiKey: BAZJVZSCDIOMDQ-MRRLEEDCSA-N

反应信息

• 作为产物：
  描述：

  2,3,5,6-tetra-O-tert-butyldimethylsilyl-1-thio-α,β-D-galactofuranose 、 溴甲苯 在 四丁基硫酸氢铵 、 碳酸氢钠 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 48.0h， 生成 benzyl 2,3,5,6-tetra-O-tert-butyldimethylsilyl-1-thio-β-D-galactofuranoside 、 benzyl 2,3,5,6-tetra-O-tert-butyldimethylsilyl-1-thio-α-D-galactofuranoside
  参考文献：
  名称：

  Synthesis of S- and C-galactofuranosides via a galactofuranosyl iodide. Isolable 1-galactofuranosylthiol derivative as a new glycosyl donor

  摘要：

  The use of the easily available persilylated derivative 1 for the synthesis of C- and S-Galf derivatives has been investigated. By anomeric iodination of 1 with TMSI, followed by in situ coupling with C-and S-nucleophiles under very mild conditions and in the absence of promoters, derivatives with value as glycomimetics or as precursors of glycobiological tools were synthesized. Among them, the synthesis of the isolable 1-galactofuranosylthiol 15 is remarkable, as it paves the way for alternative approaches for S-galactofuranosyl derivatives. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.08.021