phenylsulfenyl 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside | 1072785-92-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenylsulfenyl 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside
• CAS: 1072785-92-2
• 化学式: C₃₆H₇₂O₆SSi₄
• 分子量: 745.372
• InChiKey: BFHKQTXXOOLSET-MXBBQTRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.71
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  phenylsulfenyl 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside 、 烯丙基三甲基硅烷 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到(((2R,3S,4R,5R,6R)-2-allyl-6-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl)tris(oxy))tris(tert-butyldimethylsilane)
  参考文献：
  名称：

  Studies on the Stereoselective Synthesis of C-Allyl Glycosides

  摘要：

  An investigation was carried out to explore the use of sulfoxide donors as common precursors to stereoisomeric C-glycoconjugates of glycoprotein and glycolipid tumor antigens. A study focusing on the effects of reaction conditions and substrate structure on the stereoselectivity of allylation was carried out. Although conditions were realized to selectively afford alpha-allylation products in good to excellent yields, the search for conditions favoring beta-selectivity proved less successful.

  DOI：

  10.1021/ol801710s
• 作为产物：
  描述：

  S-phenyl 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到phenylsulfenyl 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside
  参考文献：
  名称：

  Studies on the Stereoselective Synthesis of C-Allyl Glycosides

  摘要：

  An investigation was carried out to explore the use of sulfoxide donors as common precursors to stereoisomeric C-glycoconjugates of glycoprotein and glycolipid tumor antigens. A study focusing on the effects of reaction conditions and substrate structure on the stereoselectivity of allylation was carried out. Although conditions were realized to selectively afford alpha-allylation products in good to excellent yields, the search for conditions favoring beta-selectivity proved less successful.

  DOI：

  10.1021/ol801710s