benzyl 2,3,5,6-tetra-O-tert-butyldimethylsilyl-β-D-galactofuranoside | 1130007-88-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3,5,6-tetra-O-tert-butyldimethylsilyl-β-D-galactofuranoside
• 英文别名: TBDMS(-2)[TBDMS(-3)][TBDMS(-5)][TBDMS(-6)]Galf(b)-O-Bn；[(2S,3S,4R,5R)-2-[(1R)-1,2-bis[[tert-butyl(dimethyl)silyl]oxy]ethyl]-4-[tert-butyl(dimethyl)silyl]oxy-5-phenylmethoxyoxolan-3-yl]oxy-tert-butyl-dimethylsilane
• CAS: 1130007-88-3
• 化学式: C₃₇H₇₄O₆Si₄
• 分子量: 727.333
• InChiKey: WYAOXHQEIULYJJ-MRRLEEDCSA-N

物化性质

• 沸点：
  591.8±50.0 °C(predicted)
• 密度：
  0.96±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.12
• 重原子数：
  47
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 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：

  benzyl 2,3,5,6-tetra-O-tert-butyldimethylsilyl-β-D-galactofuranoside 在 D(+)-10-樟脑磺酸 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2R,3S,4S,5R)-2-(benzyloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  Total synthesis of fuzinoside

  摘要：

  The first total syntheses of fuzinoside (1b) were achieved from o-galactose through two strategies (BCA and ABC) in 11 (total yield: 5.0%) and 15 (total yield: 3.7%) steps, respectively. Comparison of NMR data of synthetic compound 1b and those of the fuzinoside isolated from the lateral roots of Aconitum carmicaelii suggests that the structure reported in the literature(1,2) might not be accurate. The synthetic fuzinoside (1b) exhibited moderate cardiac activity in the isolated bullfrog heart assay. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.069
• 作为产物：
  描述：

  per-O-TBS-D-Galf 、 苯甲醇 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， 生成 2,3,5-tri-O-tert-butyldimethylsilyl-1,6-anhydro-α-D-galactofuranose 、 benzyl 2,3,5,6-tetra-O-tert-butyldimethylsilyl-β-D-galactofuranoside 、 benzyl 2,3,5,6-tetra-O-tert-butyldimethylsilyl-α-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.
• Total synthesis of fuzinoside
  作者：Ping He、Xiao-Huan Li、Qiao-Hong Chen、Jing-Song Yang、Feng-Peng Wang

  DOI：10.1016/j.tet.2014.04.069

  日期：2014.7

  The first total syntheses of fuzinoside (1b) were achieved from o-galactose through two strategies (BCA and ABC) in 11 (total yield: 5.0%) and 15 (total yield: 3.7%) steps, respectively. Comparison of NMR data of synthetic compound 1b and those of the fuzinoside isolated from the lateral roots of Aconitum carmicaelii suggests that the structure reported in the literature(1,2) might not be accurate. The synthetic fuzinoside (1b) exhibited moderate cardiac activity in the isolated bullfrog heart assay. (C) 2014 Elsevier Ltd. All rights reserved.