methoxymethyl O-(3,4,5-tri-O-benzyl-β-D-fructopyranosyl)-(2->1)-3,4,5-tri-O-benzyl-β-D-fructopyranoside | 880480-63-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methoxymethyl O-(3,4,5-tri-O-benzyl-β-D-fructopyranosyl)-(2->1)-3,4,5-tri-O-benzyl-β-D-fructopyranoside
• 英文别名: [(2S,3S,4R,5R)-2-[[(2S,3S,4R,5R)-2-(methoxymethoxy)-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanol
• CAS: 880480-63-7
• 化学式: C₅₆H₆₂O₁₂
• 分子量: 927.101
• InChiKey: RAWWOXIDJRPJOW-UPAJAPDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  68
• 可旋转键数：
  25
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1-O-acetyl-3,4,5-tri-O-benzyl-β-D-fructopyranosyl fluoride 、 methoxymethyl O-(3,4,5-tri-O-benzyl-β-D-fructopyranosyl)-(2->1)-3,4,5-tri-O-benzyl-β-D-fructopyranoside 在 4 A molecular sieve 、 zirconocene dichloride 、 silver perchlorate 作用下， 以 二氯甲烷 为溶剂， 以22.2%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 O-(1-O-acetyl-3,4,5-tri-O-benzyl-β-D-fructopyranosyl)-(2->1)-3,4,5-tri-O-benzyl-β-D-fructopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以90.8%的产率得到methoxymethyl O-(3,4,5-tri-O-benzyl-β-D-fructopyranosyl)-(2->1)-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