[(2R,3R,4R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)-5-hydroxyoxolan-2-yl]methyl benzoate | 1232836-55-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3R,4R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)-5-hydroxyoxolan-2-yl]methyl benzoate
• CAS: 1232836-55-3
• 化学式: C₃₄H₂₈O₁₀
• 分子量: 596.59
• InChiKey: ZYJUUZKDMZKDIS-FINVSBJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  44.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  134.66
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)-5-hydroxyoxolan-2-yl]methyl benzoate 在 正丁基锂 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成
  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
• 作为产物：
  描述：

  D-psicofuranose 、 苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以67%的产率得到[(2R,3R,4R)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)-5-hydroxyoxolan-2-yl]methyl benzoate
  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

• Synthesis of Sucrose-Mimicking Disaccharide by Intramolecular Aglycone Delivery
  作者：Kanae Sano、Akihiro Ishiwata、Hiroto Takamori、Takashi Kikuma、Katsunori Tanaka、Yukishige Ito、Yoichi Takeda

  DOI：10.3390/molecules29081771

  日期：——

  performed using a psicofuranosyl acceptor with 1,3,4,6-tetra-O-benzoyl groups. This is the first report on the synthesis of non-reducing disaccharides comprising only rare d-sugars by IAD using protected ketose as a unique acceptor; additionally, this approach is expected to be applicable to the synthesis of functional sweeteners.

  稀有糖因其抑制餐后血糖水平的能力而闻名。因此，源自稀有糖的低聚糖和二糖有可能作为功能性甜味剂。由稀有单糖 D-阿洛糖和 D-阿洛酮糖合成了一种模仿蔗糖的二糖 [α-d-吡喃糖基-(1→2)-β-d-阿洛酮呋喃苷]。采用分子间苷元递送（IAD）方法进行糖基化，选择性地形成别吡喃糖残基的1,2-顺式α-糖苷键。此外，使用具有 1,3,4,6-四-O-苯甲酰基的 psicofuranosyl 受体进行 β-选择性 psicofuranosylation。这是第一篇关于通过 IAD 使用受保护的酮糖作为独特受体合成仅包含稀有 d-糖的非还原性二糖的报道；此外，该方法有望适用于功能性甜味剂的合成。
• 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.