2,6-anhydro-3,4-di-O-benzoyl-1-deoxy-5-O-(2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl)-D-arabino-hex-1-enitol | 131157-74-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,6-anhydro-3,4-di-O-benzoyl-1-deoxy-5-O-(2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl)-D-arabino-hex-1-enitol
• CAS: 131157-74-9
• 化学式: C₅₄H₄₄O₁₅
• 分子量: 932.934
• InChiKey: NMSKPKQFZHMJSB-OVRZSFIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.63
• 重原子数：
  69.0
• 可旋转键数：
  15.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  185.49
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  2,6-anhydro-3,4-di-O-benzoyl-1-deoxy-5-O-(2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl)-D-arabino-hex-1-enitol 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 以53%的产率得到1,5-anhydro-3,4-di-O-benzoyl-6-deoxy-2-O-(2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl)-D-mannitol
  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：

  1,3,4-tri-O-benzoyl-5-O-(2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl)-β-D-fructopyranose 在 氢溴酸 、 sodium acetate 、 copper(II) sulfate 、 锌 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 8.0h， 生成 2,6-anhydro-3,4-di-O-benzoyl-1-deoxy-5-O-(2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl)-D-arabino-hex-1-enitol
  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