1,3,4-tri-O-acetyl-5-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-fructopyranose | 131157-82-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4-tri-O-acetyl-5-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-fructopyranose
• CAS: 131157-82-9
• 化学式: C₂₆H₃₆O₁₈
• 分子量: 636.561
• InChiKey: YGZGOWNZFHFQPC-ALDHFOERSA-N

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1,3,4-tri-O-acetyl-5-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-fructopyranose 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 12.0h， 生成 1,2,3,4-tetra-O-acetyl-5-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-fructopyranose 、 1,3,4,6-tetra-O-acetyl-5-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-D-fructose
  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：

  leucrose (O-α-D-glucopyranosyl-(1-5)-D-fructopyranose) 、 乙酸酐 在 吡啶 作用下， 以74%的产率得到1,3,4-tri-O-acetyl-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