methyl 2,3,4-tri-O-benzyl-6,6,6-trifluoro-α-L-rhamnopyranosyl-(1->4)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6,6,6-trifluoro-α-L-rhamnopyranosyl-(1->4)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: (2S,3R,4S,5R,6R)-2-methoxy-3,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-5-[(2R,3R,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(trifluoromethyl)oxan-2-yl]oxyoxane
• 化学式: C₅₅H₅₇F₃O₁₀
• 分子量: 935.047
• InChiKey: FNTQOSPUSKLDIB-MPPLJHQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  68
• 可旋转键数：
  22
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  S-phenyl 2,3,4-tri-O-benzyl-6,6,6-trifluoro-β-L-thiorhamnopyranoside 、 甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 在 3 A molecular sieve 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 以38%的产率得到methyl 2,3,4-tri-O-benzyl-6,6,6-trifluoro-β-L-rhamnopyranosyl-(1->4)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Glycosylation of a Series of 6-Mono-, Di-, and Trifluoro S-Phenyl 2,3,4-Tri-O-benzyl-thiorhamnopyranosides. Effect of the Fluorine Substituents on Glycosylation Stereoselectivity

  摘要：

  A series of 6-mono-, di-, and trifluoro analogs of S-phenyl 2,3,4-tri-O-benzyl-D- or L-thiorhamnopyranoside has been synthesized and used as donors in glycosylation reactions, with activation by the 1-benzenesulfinyl pipe ridine/triflic anhydride system. The stereochemical outcome of the glycosylation reactions was found to depend on the electron-withdrawing capability of the disarming substituent at the 6-position, i.e., on the number of fluorine atoms present. The results are explained with regard to the increased stability of the glycosyl triflates, shown to be intermediates in the reaction by low-temperature H-1 NMR experiments, with increased fluorine content.

  DOI：

  10.1021/ja0730258

文献信息

• Synthesis and Glycosylation of a Series of 6-Mono-, Di-, and Trifluoro <i>S</i>-Phenyl 2,3,4-Tri-<i>O</i>-benzyl-thiorhamnopyranosides. Effect of the Fluorine Substituents on Glycosylation Stereoselectivity
  作者：David Crich、Olga Vinogradova

  DOI：10.1021/ja0730258

  日期：2007.9.1

  A series of 6-mono-, di-, and trifluoro analogs of S-phenyl 2,3,4-tri-O-benzyl-D- or L-thiorhamnopyranoside has been synthesized and used as donors in glycosylation reactions, with activation by the 1-benzenesulfinyl pipe ridine/triflic anhydride system. The stereochemical outcome of the glycosylation reactions was found to depend on the electron-withdrawing capability of the disarming substituent at the 6-position, i.e., on the number of fluorine atoms present. The results are explained with regard to the increased stability of the glycosyl triflates, shown to be intermediates in the reaction by low-temperature H-1 NMR experiments, with increased fluorine content.