methyl 2,3,5,6-tetra-O-tert-butyldimethylsilyl-β-D-galactofuranosyl-(1->3)-2-O-benzoyl-5,6-O-isopropylidene-β-D-galactofuranoside | 1130007-99-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,5,6-tetra-O-tert-butyldimethylsilyl-β-D-galactofuranosyl-(1->3)-2-O-benzoyl-5,6-O-isopropylidene-β-D-galactofuranoside
• 英文别名: [(2R,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-methoxyoxolan-3-yl] benzoate
• CAS: 1130007-99-6
• 化学式: C₄₇H₈₈O₁₂Si₄
• 分子量: 957.551
• InChiKey: CGOQWRRADBWSHN-AZHIFYJDSA-N

物化性质

• 沸点：
  737.8±60.0 °C(predicted)
• 密度：
  1.05±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.04
• 重原子数：
  63
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  methyl 2-O-benzoyl-5,6-O-isopropylidene-β-D-galactofuranoside 、 per-O-TBS-D-Galf 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79%的产率得到methyl 2,3,5,6-tetra-O-tert-butyldimethylsilyl-β-D-galactofuranosyl-(1->3)-2-O-benzoyl-5,6-O-isopropylidene-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

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.