(2S,3S,4R,5S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)-2-(p-tolyl-thio)tetrahydrofuran-3-yl benzoate | 1374633-04-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)-2-(p-tolyl-thio)tetrahydrofuran-3-yl benzoate
• 英文别名: p-tolyl 2-O-benzoyl-3-O-levulinoyl-5,6-O-isopropylidene-1-thio-β-d-galactofuranoside；[(2S,3R,4S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(4-methylphenyl)sulfanyl-4-(4-oxopentanoyloxy)oxolan-3-yl] benzoate
• CAS: 1374633-04-1
• 化学式: C₂₈H₃₂O₈S
• 分子量: 528.623
• InChiKey: LXNDLWWTTPSASO-VGCAIQGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)-2-(p-tolyl-thio)tetrahydrofuran-3-yl benzoate 在 N-碘代丁二酰亚胺 、 乙酸肼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 (2R,3S,4R,5R)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxy-2-(2-phenyl-1,3-dioxan-5-yloxy)tetrahydrofuran-3-yl benzoate
  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：

  p-tolyl 5,6-O-isopropylidene-1-thio-β-D-galactofuranoside 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2S,3S,4R,5S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)-2-(p-tolyl-thio)tetrahydrofuran-3-yl benzoate
  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

文献信息

• Synthesis of tetra- and hexasaccharide fragments corresponding to the O-antigenic polysaccharide of Klebsiella pneumoniae
  作者：San-Yong Zhu、Jin-Song Yang

  DOI：10.1016/j.tet.2012.03.074

  日期：2012.5

  The preparation of linear tetra- (1) and hexasaccharides (2), containing the repeating unit [-> 3)-beta-Galf-(1 -> 3)-alpha-Galp-(1 -> ] present in the O-polysaccharide of the lipopolysaccharide of Klebsiella pneumoniae is described. The key step in their synthesis is the alpha-selective galactopyranosylation of 3-OH di- and tetrasaccharide acceptors (20 and 22) with a disaccharide trichloroacetimidate donor 19 in the presence of trimethylsilyl triflate in a diethyl ether-CH2Cl2 mixture as solvent. (C) 2012 Elsevier Ltd. All rights reserved.