methoxymethyl 3,4,5-tri-O-benzyl-β-D-fructopyranoside | 880480-57-9

• 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: methoxymethyl 3,4,5-tri-O-benzyl-β-D-fructopyranoside
• 英文别名: 2-O-methoxymethyl 3,4,5-tri-O-benzyl-β-D-fructopyranoside；[(2S,3S,4R,5R)-2-(methoxymethoxy)-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanol
• CAS: 880480-57-9
• 化学式: C₂₉H₃₄O₇
• 分子量: 494.585
• InChiKey: PKLWKIBZAQSXOO-GKQHHHCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methoxymethyl 3,4,5-tri-O-benzyl-β-D-fructopyranoside 在 palladium on activated charcoal 4 A molecular sieve 、 氢气 、 silver perchlorate 、 溶剂黄146 、 tin(ll) chloride 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 20.0 ℃ 、310.01 kPa 条件下， 反应 26.5h， 生成 α-D-fructopyranose β-D-fructopyranose 1,2':2,1'-dianhydride
  参考文献：
  名称：

  Catalytic, Stereoselective Glycosylation - Spiroketalization of 3,4,5-Tri-O-benzyl-b-D-fructopyranose Generating Di-D-fructopyranose- 1,2’:2,1’-dianhydride

  摘要：

  alpha-D-Fructopyranose beta-D-fructopyranose-1,2':2,1'-dianhydride has been stereoselectively synthesized by tandem catalytic glycosylation-spiroketalization of 3,4,5-tri-O-benzyl-beta-D-fructo- pyranose. Of the several protic acid catalysts which exist, 0.3 molar equivalent trifluoromethane sulfonic acid in toluene was found to be most effective to afford the dianhydride in good yield.

  DOI：

  10.3987/com-06-s(o)50
• 作为产物：
  描述：

  1-O-acetyl-3,4,5-tri-O-benzyl-β-D-fructopyranose 在 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成 methoxymethyl 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

文献信息

• Synthesis of Di- and Trisaccharides Comprising D-Fructopyranose with β2 → 1 Glycosidic Linkage Using β-D-Fructopyranosyl Fluoride as the Fructosyl Donor
  作者：Eisuke Kaji、Emiko Kurimoto、Reiko Saiga、Ayako Matsuura、Kazuho Harada、Takashi Nishino

  DOI：10.3987/com-05-s(k)54

  日期：——

  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.
• Catalytic, Stereoselective Glycosylation - Spiroketalization of 3,4,5-Tri-O-benzyl-b-D-fructopyranose Generating Di-D-fructopyranose- 1,2’:2,1’-dianhydride
  作者：Eisuke Kaji、Reiko Saiga、Emiko Kurimoto、Takashi Nishino

  DOI：10.3987/com-06-s(o)50

  日期：——

  alpha-D-Fructopyranose beta-D-fructopyranose-1,2':2,1'-dianhydride has been stereoselectively synthesized by tandem catalytic glycosylation-spiroketalization of 3,4,5-tri-O-benzyl-beta-D-fructo- pyranose. Of the several protic acid catalysts which exist, 0.3 molar equivalent trifluoromethane sulfonic acid in toluene was found to be most effective to afford the dianhydride in good yield.