2,3,5,6-tetra-O-tert-butyldimethylsilyl-β-D-galactofuranosyl-(1->3)-2-O-benzoyl-5,6-diisopropylidene-D-galactono-1,4-lactone | 1130007-91-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5,6-tetra-O-tert-butyldimethylsilyl-β-D-galactofuranosyl-(1->3)-2-O-benzoyl-5,6-diisopropylidene-D-galactono-1,4-lactone
• 英文别名: [(3R,4S,5S)-4-[(2R,3R,4S,5S)-5-[(1R)-1,2-bis[[tert-butyl(dimethyl)silyl]oxy]ethyl]-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]oxolan-2-yl]oxy-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxooxolan-3-yl] benzoate
• CAS: 1130007-91-8
• 化学式: C₄₆H₈₄O₁₂Si₄
• 分子量: 941.508
• InChiKey: YCVZLIKQQOZSPO-FSPZFALBSA-N

物化性质

• 沸点：
  750.0±60.0 °C(predicted)
• 密度：
  1.06±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.59
• 重原子数：
  62
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2,3,5,6-tetra-O-tert-butyldimethylsilyl-β-D-galactofuranosyl-(1->3)-2-O-benzoyl-5,6-diisopropylidene-D-galactono-1,4-lactone 在 diisoamyl borane 作用下， 以 四氢呋喃 为溶剂， 生成 2,3,5,6-tetra-O-tert-butyldimethylsilyl-β-D-galactofuranosyl-(1->3)-2-O-benzoyl-5,6-diisopropylidene-β-D-galactofuranose 、 2,3,5,6-tetra-O-tert-butyldimethylsilyl-β-D-galactofuranosyl-(1->3)-2-O-benzoyl-5,6-diisopropylidene-α-D-galactofuranose
  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
• 作为产物：
  描述：

  per-O-TBS-D-Galf 、 2-O-benzoyl-5,6-O-isopropylidene-D-galactono-1,4-lactone 在 碘代三甲硅烷 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到2,3,5,6-tetra-O-tert-butyldimethylsilyl-β-D-galactofuranosyl-(1->3)-2-O-benzoyl-5,6-diisopropylidene-D-galactono-1,4-lactone
  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.