(2S,3S)-1-bromo-2-((2R,4R,5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl)-7-(trimethylsilyl)hept-6-yne-2,3,4-triol | 1042419-74-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S)-1-bromo-2-((2R,4R,5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl)-7-(trimethylsilyl)hept-6-yne-2,3,4-triol
• CAS: 1042419-74-8
• 化学式: C₂₀H₂₉BrO₆Si
• 分子量: 473.436
• InChiKey: QGORAQGPTQFWMR-CKBJSLFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  99.38
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  3-C-(bromomethyl)-D-allopyranose 、 3-溴-1-三甲基硅基-1-丙炔 、 苯甲醛二甲缩醛 在 1,1-二溴乙烷 、 magnesium 、 对甲苯磺酸 、 cerium(III) chloride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 四氢呋喃 为溶剂， 反应 17.0h， 生成 (2S,3S)-1-bromo-2-((2R,4R,5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl)-7-(trimethylsilyl)hept-6-yne-2,3,4-triol
  参考文献：
  名称：

  Syntheses of Branched Non‐1‐ynitols by Chemoselective Addition of (Trimethylsilyl)‐propargylmagnesium Bromide at the Anomeric Center of Side Chain Halogeno Functionalized Carbohydrates

  摘要：

  A convenient method for the syntheses of non-1-ynitols 8a-8d, by chemoselective addition of (trimethylsilyl)-propargylmagnesium bromide at the anomeric center of a 1-unprotected sugar, in the presence of 3-C'-halide and 3-C'-silyl functions in the side chain is described. In addition, an efficient method for the synthesis of 3-C'-hydroxymethyl sugar 3 via the addition of C1 silyl Grignard reagents to ulose 1 and subsequent oxidation by the Fleming-Tamao method in excellent yields is reported. Also, a suitable acid-catalyzed isomerization of the 1,2-O-isopropylidene group to the 2,3-O-isopropylidene group (5a-5f), to get access to the anomeric center, in good to excellent yields has been depicted.

  DOI：

  10.1080/07328300801991278