(2R,3R,4R,5R)-2,5-bis((benzoyloxy)methyl)-2-phenethoxytetrahydrofuran-3,4-diyl dibenzoate | 1232836-61-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R,3R,4R,5R)-2,5-bis((benzoyloxy)methyl)-2-phenethoxytetrahydrofuran-3,4-diyl dibenzoate
• CAS: 1232836-61-1
• 化学式: C₄₂H₃₆O₁₀
• 分子量: 700.742
• InChiKey: NHYVFEJXAQHYCQ-QTJTVSACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.51
• 重原子数：
  52.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  苯甲酰氯 在 吡啶 、 calcium sulfate 、 正丁基锂 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2S,3R,4R,5R)-2,5-bis((benzoyloxy)methyl)-2-phenethoxytetrahydrofuran-3,4-diyl dibenzoate 、 (2R,3R,4R,5R)-2,5-bis((benzoyloxy)methyl)-2-phenethoxytetrahydrofuran-3,4-diyl dibenzoate
  参考文献：
  名称：

  Stereoselectivity of D-Psicofuranosylation Influenced by Protecting Groups of Psicofuranosyl Donors

  摘要：

  We synthesized several types of novel D-psicofuranosyl acetate derivatives, and investigated their use as glycosyl donors in scandium triflate-catalyzed D-psicofuranosylation reactions. Psicofuranosylation demonstrated unique stereoselectivities depending on the protecting groups of psicofuranosyl donors. The donor having a 3,4-isopropylidene group afforded beta-psicofuranosides with high stereoselectivities. Donors having a C3 benzoyloxy group demonstrated low stereoselectivities with no neighboring group participation. This study also discusses the stereoselectivities of psicofuranosylation based on the conformers of the glycosyl oxocarbenium ion intermediates as influenced by the protecting groups of the psicofuranosyl donors. We also compared the neighboring group participation of the glycosyl donors bearing a C3 benzoyloxy group during D-psicofuranosylation and D-fructofuranosylation.

  DOI：

  10.3987/com-15-s(t)39

文献信息

• L-Fructo- and D-Psicofuranosylation Reactions Catalyzed by Scandium Triflate
  作者：Takashi Yamanoi、Toshiaki Ishiyama、Yoshiki Oda、Sho Matsuda、Mikio Watanabe

  DOI：10.3987/com-10-11916

  日期：——

  This paper describes the formation of L-fructo- and D-psicofuranosidic bonds by the scandium triflate catalyzed glycosidation. The reaction of the benzoylated L-fructofuranosyl acetate with an alcohol in the presence of 5 mol% scandium triflate in toluene at room temperature for 3 h stereoselectively afforded the corresponding alpha-L-fructofuranoside in good yields. Several alpha-D-psicofuranosides were predominantly obtained in good yields by the reactions between the benzoylated D-psicofuranosyl acetate and alcohols under similar reaction conditions. This method successfully provided the sucrose mimics composed of D-glucopyranose and L-fructofuranose or D-psicofuranose.