3,4-di-O-acetyl-5-O-(2,3-di-O-acetyl-α-D-glucopyranosyl)-1,2-O-isopropylidene-β-D-fructopyranose | 131157-85-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-di-O-acetyl-5-O-(2,3-di-O-acetyl-α-D-glucopyranosyl)-1,2-O-isopropylidene-β-D-fructopyranose
• 英文别名: [(5S,6S,7R,8R)-6-acetyloxy-8-[(2R,3R,4S,5R,6R)-3,4-diacetyloxy-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,2-dimethyl-1,3,10-trioxaspiro[4.5]decan-7-yl] acetate
• CAS: 131157-85-2
• 化学式: C₂₃H₃₄O₁₅
• 分子量: 550.514
• InChiKey: FUBAIMICVSZMLE-ICYJOLOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  192
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 3,4-di-O-acetyl-5-O-(2,3-di-O-acetyl-α-D-glucopyranosyl)-1,2-O-isopropylidene-β-D-fructopyranose 在 吡啶 作用下， 以97%的产率得到3,4-di-O-acetyl-1,2-O-isopropylidene-5-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-fructopyranose
  参考文献：
  名称：

  Synthesis and reactions of leucrose and its exocyclic glycal

  摘要：

  5-O-alpha-D-Glucopyranosyl-beta-D-fructopyranose (leucrose, 1) was transformed into 3,4-di-O-acetyl-1-O-methanesulfonyl-5-O-(2,3,4-tri-O-acetyl-6-O-methanes ulfonyl-alpha-D-glucopyranosyl)-beta-D-fructopyranosyl bromide (3) and 1,3,4-tri-O-benzoyl-5-O-(2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl) -beta-D-fructopyranosyl bromide (8), which were converted into derivatives (8 and 9) of 2,6-anhydro-1-deoxy-5-O-alpha-D-glucopyranosyl-D-arabino-hex-1-enitol . Hydrogenation of 8 and 9 gave the corresponding anhydroalditol derivatives. N-Iodosuccinimide-mediated glycosylation of 9 with 1,2,3,4-tetra-O-acetyl-beta-D-glucopyranose gave 1,2,3,4-tetra-O-acetyl-6-O-[3,4-di-O-benzyl-1-deoxy-1-iodo-5-O-(2,3,4,6- tetra-O-benzoyl-alpha-D-glucopyranosyl)-beta-D-fructopyranosyl]- beta-D-glucopyranose (12). Some amino, acetylated, and isopropylidene derivatives of leucrose have been prepared and characterised.

  DOI：

  10.1016/0008-6215(90)80151-r
• 作为产物：
  描述：

  3,4-di-O-acetyl-5-O-(2,3-di-O-acetyl-4,6-O-isopropylidene-α-D-glucopyranosyl)-1,2-O-isopropylidene-β-D-fructopyranose 在 silica gel 、 三氯化铁 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以74%的产率得到3,4-di-O-acetyl-5-O-(2,3-di-O-acetyl-α-D-glucopyranosyl)-1,2-O-isopropylidene-β-D-fructopyranose
  参考文献：
  名称：

  Synthesis and reactions of leucrose and its exocyclic glycal

  摘要：

  5-O-alpha-D-Glucopyranosyl-beta-D-fructopyranose (leucrose, 1) was transformed into 3,4-di-O-acetyl-1-O-methanesulfonyl-5-O-(2,3,4-tri-O-acetyl-6-O-methanes ulfonyl-alpha-D-glucopyranosyl)-beta-D-fructopyranosyl bromide (3) and 1,3,4-tri-O-benzoyl-5-O-(2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl) -beta-D-fructopyranosyl bromide (8), which were converted into derivatives (8 and 9) of 2,6-anhydro-1-deoxy-5-O-alpha-D-glucopyranosyl-D-arabino-hex-1-enitol . Hydrogenation of 8 and 9 gave the corresponding anhydroalditol derivatives. N-Iodosuccinimide-mediated glycosylation of 9 with 1,2,3,4-tetra-O-acetyl-beta-D-glucopyranose gave 1,2,3,4-tetra-O-acetyl-6-O-[3,4-di-O-benzyl-1-deoxy-1-iodo-5-O-(2,3,4,6- tetra-O-benzoyl-alpha-D-glucopyranosyl)-beta-D-fructopyranosyl]- beta-D-glucopyranose (12). Some amino, acetylated, and isopropylidene derivatives of leucrose have been prepared and characterised.

  DOI：

  10.1016/0008-6215(90)80151-r

文献信息

• THIEM, JOACHIM;KLEEBERG, MATTHIAS, CARBOHYDR. RES., 205,(1990) C. 333-345
  作者：THIEM, JOACHIM、KLEEBERG, MATTHIAS

  DOI：——

  日期：——