3,4-di-O-acetyl-1-O-methanesulfonyl-5-O-(2,3,4-tri-O-acetyl-6-O-methanesulfonyl-α-D-glucopyranosyl)-β-D-fructopyranose | 131157-67-0

• 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-1-O-methanesulfonyl-5-O-(2,3,4-tri-O-acetyl-6-O-methanesulfonyl-α-D-glucopyranosyl)-β-D-fructopyranose
• CAS: 131157-67-0
• 化学式: C₂₄H₃₆O₂₀S₂
• 分子量: 708.67
• InChiKey: JAYQKSDETFJSDO-VBWXRZLCSA-N

反应信息

• 作为反应物：
  描述：

  3,4-di-O-acetyl-1-O-methanesulfonyl-5-O-(2,3,4-tri-O-acetyl-6-O-methanesulfonyl-α-D-glucopyranosyl)-β-D-fructopyranose 在 氢溴酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 5.0h， 以72%的产率得到3,4-di-O-acetyl-1-O-methanesulfonyl-5-O-(2,3,4-tri-O-acetyl-6-O-methanesulfonyl-α-D-glucopyranosyl)-β-D-fructopyranosyl bromide
  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：

  乙酸酐 、 Methanesulfonic acid (2R,3S,4S,5R)-2,3,4-trihydroxy-5-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methanesulfonyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester 在 吡啶 作用下， 生成 3,4-di-O-acetyl-1-O-methanesulfonyl-5-O-(2,3,4-tri-O-acetyl-6-O-methanesulfonyl-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