n-butyl 2,3,5,6-tetra-O-tert-butyldimethylsilyl-D-galactofuranoside | 1130007-86-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: n-butyl 2,3,5,6-tetra-O-tert-butyldimethylsilyl-D-galactofuranoside
• 英文别名: TBDMS(-2)[TBDMS(-3)][TBDMS(-5)][TBDMS(-6)]Galf-O-Bu；[(2S,3S,4R)-2-[(1R)-1,2-bis[[tert-butyl(dimethyl)silyl]oxy]ethyl]-5-butoxy-4-[tert-butyl(dimethyl)silyl]oxyoxolan-3-yl]oxy-tert-butyl-dimethylsilane
• CAS: 1130007-86-1
• 化学式: C₃₄H₇₆O₆Si₄
• 分子量: 693.316
• InChiKey: NDGGOKFCIHUIQV-LSZMOXLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.72
• 重原子数：
  44
• 可旋转键数：
  18
• 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

• 作为反应物：
  描述：

  n-butyl 2,3,5,6-tetra-O-tert-butyldimethylsilyl-D-galactofuranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 n-butyl α-D-galactofuranoside 、 n-butyl β-D-galactofuranoside
  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