1,3,4,5-tetra-O-benzoyl-β-D-fructopyranosyl-(2→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside

• 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: 1,3,4,5-tetra-O-benzoyl-β-D-fructopyranosyl-(2→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside
• 英文别名: [(2R,3S,4R,5R)-3,4,5-tribenzoyloxy-2-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-2-yl]methyl benzoate
• 化学式: C₄₆H₄₆O₁₅
• 分子量: 838.862
• InChiKey: AMECAEIPSWJPAL-TXLFSPAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  61
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  1,3,4,5-tetra-O-benzoyl-β-D-fructopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 1,3,4,5-tetra-O-benzoyl-β-D-fructopyranosyl-(2→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of d-fructopyranosides with 2-O-acyl-β-d-fructopyranosides

  摘要：

  Glycosylation of 2-O-acyl fructopyranosides was investigated, which were shown to be effective glycosyl donors for D-fructopyranoside synthesis with good beta-selectivity and yields. For bulky acceptor 4e, alpha-anomer 5e was obtained with alpha/beta = 65:23. Unexpected ring-opening was observed during acetylation of 9, indicating the sensitivity of the fructopyranosyl ring. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.128

文献信息

• Synthesis of d-fructopyranosides with 2-O-acyl-β-d-fructopyranosides
  作者：Feng Lin、Qiulong Xu、Rui Lu、Liqun Yue

  DOI：10.1016/j.tetlet.2013.10.128

  日期：2014.1

  Glycosylation of 2-O-acyl fructopyranosides was investigated, which were shown to be effective glycosyl donors for D-fructopyranoside synthesis with good beta-selectivity and yields. For bulky acceptor 4e, alpha-anomer 5e was obtained with alpha/beta = 65:23. Unexpected ring-opening was observed during acetylation of 9, indicating the sensitivity of the fructopyranosyl ring. (C) 2013 Elsevier Ltd. All rights reserved.