1,2,3,4,6-penta-O-tert-butyldimethylsilyl-β-D-galactopyranose | 1130007-83-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2,3,4,6-penta-O-tert-butyldimethylsilyl-β-D-galactopyranose
• 英文别名: TBDMS(-2)[TBDMS(-3)][TBDMS(-4)][TBDMS(-6)]Gal(b)-O-TBDMS；tert-butyl-dimethyl-[[(2R,3S,4S,5R,6S)-3,4,5,6-tetrakis[[tert-butyl(dimethyl)silyl]oxy]oxan-2-yl]methoxy]silane
• CAS: 1130007-83-8
• 化学式: C₃₆H₈₂O₆Si₅
• 分子量: 751.471
• InChiKey: QAVJXXJHDMBKDU-NBCLCUQJSA-N

物化性质

• 沸点：
  587.1±50.0 °C(predicted)
• 密度：
  0.92±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.93
• 重原子数：
  47
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  D-吡喃葡萄糖 、 叔丁基二甲基氯硅烷 在 吡啶 、 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以45%的产率得到per-O-TBS-D-Galf
  参考文献：
  名称：

  Facile Synthesis of per-O-tert-Butyldimethylsilyl-β-d-galactofuranose and Efficient Glycosylation via the Galactofuranosyl Iodide

  摘要：

  The synthesis of crystalline per-O-TBS-beta-D-galactofuranose (4 beta) as a new precursor of D-Galf units is described. Anomeric iodination by reaction with TMSI followed by in situ coupling with simple alcohols and a wide variety of glycosyl acceptors, in the absence of a promoter, was employed as a new efficient glycosylation method for the assembly Of D-galactofuranosyl moieties with high beta-stereoselectivity. Under the mild conditions of this reaction labile protective groups, like acetals, and furanosyl linkages are preserved.

  DOI：

  10.1021/jo8025274

文献信息

• Facile Synthesis of per-<i>O-tert</i>-Butyldimethylsilyl-β-<scp>d</scp>-galactofuranose and Efficient Glycosylation via the Galactofuranosyl Iodide
  作者：Luciana Baldoni、Carla Marino

  DOI：10.1021/jo8025274

  日期：2009.3.6

  The synthesis of crystalline per-O-TBS-beta-D-galactofuranose (4 beta) as a new precursor of D-Galf units is described. Anomeric iodination by reaction with TMSI followed by in situ coupling with simple alcohols and a wide variety of glycosyl acceptors, in the absence of a promoter, was employed as a new efficient glycosylation method for the assembly Of D-galactofuranosyl moieties with high beta-stereoselectivity. Under the mild conditions of this reaction labile protective groups, like acetals, and furanosyl linkages are preserved.