O-(1-O-acetyl-3,4,5-tri-O-benzyl-β-D-fructopyranosyl)-(2->1)-3,4,5-tri-O-benzyl-β-D-fructopyranosyl fluoride | 880480-69-3

• 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: O-(1-O-acetyl-3,4,5-tri-O-benzyl-β-D-fructopyranosyl)-(2->1)-3,4,5-tri-O-benzyl-β-D-fructopyranosyl fluoride
• 英文别名: Bn(-3)[Bn(-4)][Bn(-5)]Fru1Ac(b2-1)[Bn(-3)][Bn(-4)][Bn(-5)]a-Fru2F；[(2S,3S,4R,5R)-2-[[(2S,3S,4R,5R)-2-fluoro-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl acetate
• CAS: 880480-69-3
• 化学式: C₅₆H₅₉FO₁₁
• 分子量: 927.076
• InChiKey: BCPANVHDFYREOZ-SLXMXYGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  68
• 可旋转键数：
  24
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methoxymethyl 3,4,5-tri-O-benzyl-β-D-fructopyranoside 、 O-(1-O-acetyl-3,4,5-tri-O-benzyl-β-D-fructopyranosyl)-(2->1)-3,4,5-tri-O-benzyl-β-D-fructopyranosyl fluoride 在 4 A molecular sieve 、 zirconocene dichloride 、 silver perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以19.8%的产率得到methoxymethyl O-(1-O-acetyl-3,4,5-tri-O-benzyl-β-D-fructopyranosyl)-(2->1)-(3,4,5-tri-O-benzyl-β-D-fructopyranosyl)-(1->2)-3,4,5-tri-O-benzyl-β-D-fructopyranoside
  参考文献：
  名称：

  Synthesis of Di- and Trisaccharides Comprising D-Fructopyranose with β2 → 1 Glycosidic Linkage Using β-D-Fructopyranosyl Fluoride as the Fructosyl Donor

  摘要：

  D-Fructose was converted into a stable, suitably protected fructosyl donor for iterative glycosylation, i.e., 1-O-acetyl-3,4,5-tri-O-benzyl-beta-D-fructoyranosyl fluoride and a fructosyl acceptor, methoxymethyl 3,4,5-tri-O-benzyl-beta-D-fructopyranoside in good yields. Glycosylation of the both substrates provided di- and trisaccharides comprising beta-D-fructopyranose with beta (2 -> 1)-interglycosidic linkage.

  DOI：

  10.3987/com-05-s(k)54
• 作为产物：
  描述：

  methoxymethyl 3,4,5-tri-O-benzyl-β-D-fructopyranoside 在 三甲基溴硅烷 、 4 A molecular sieve 、 zirconocene dichloride 、 silver perchlorate 作用下， 以 二氯甲烷 为溶剂， 反应 3.75h， 生成 O-(1-O-acetyl-3,4,5-tri-O-benzyl-β-D-fructopyranosyl)-(2->1)-3,4,5-tri-O-benzyl-β-D-fructopyranosyl fluoride
  参考文献：
  名称：

  Synthesis of Di- and Trisaccharides Comprising D-Fructopyranose with β2 → 1 Glycosidic Linkage Using β-D-Fructopyranosyl Fluoride as the Fructosyl Donor

  摘要：

  D-Fructose was converted into a stable, suitably protected fructosyl donor for iterative glycosylation, i.e., 1-O-acetyl-3,4,5-tri-O-benzyl-beta-D-fructoyranosyl fluoride and a fructosyl acceptor, methoxymethyl 3,4,5-tri-O-benzyl-beta-D-fructopyranoside in good yields. Glycosylation of the both substrates provided di- and trisaccharides comprising beta-D-fructopyranose with beta (2 -> 1)-interglycosidic linkage.

  DOI：

  10.3987/com-05-s(k)54