methyl-4',6'-O-phenylboronate-β-D-cellobioside | 1213789-32-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-4',6'-O-phenylboronate-β-D-cellobioside
• 英文别名: Me-^4',6'(PhB)-β-D-clb；(4aR,6S,7R,8R,8aS)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxaborinine-7,8-diol
• CAS: 1213789-32-2
• 化学式: C₁₉H₂₇BO₁₁
• 分子量: 442.228
• InChiKey: DQGIQSKSKNZLPI-HBQZOLMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.29
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  157
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  甲基 4-O-beta-D-吡喃葡萄糖基-beta-D-吡喃葡萄糖苷 、 苯硼酸 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以95%的产率得到methyl-4',6'-O-phenylboronate-β-D-cellobioside
  参考文献：
  名称：

  Studies on the boronation of methyl-β-d-cellobioside—a cellulose model

  摘要：

  The conversion of phenylboronic acid (PBA) with methyl-beta-D-cellobioside (Me-beta-D-clb) and cellodextrins (DPw 12) was investigated to gain a basic understanding of the interactions of boric acid derivatives with oligo- and polyglucans. By means of MS and NMR experiments, it was possible to show a first stage formation of a six-membered ring at C-4 and C-6 of the non-reducing glucose occurs as in the case of mono-saccharides. If the amount of reagent is increased the formation of seven-membered rings at the secondary OH moieties is observed. Even the existence of two of these large ring-systems in the direct neighborhood was found. Application of an excess of boronation reagent led to dimerization reactions of Me-beta-D-clb via the primary reducing glucose residue as confirmed by DOSY NMR studies. Preliminary C-13 NMR studies for the interaction of cellodextrins with PBA in DMSO solution confirmed a functionalization at the trans-1,2-diol moieties of these oligomers. The amount of reagent applied may either was shown to lead to soluble products or to insoluble cross-linked material. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.11.007

文献信息

• Studies on the boronation of methyl-β-d-cellobioside—a cellulose model
  作者：Marcel Meiland、Thomas Heinze、Wolfgang Guenther、Tim Liebert

  DOI：10.1016/j.carres.2009.11.007

  日期：2010.1

  The conversion of phenylboronic acid (PBA) with methyl-beta-D-cellobioside (Me-beta-D-clb) and cellodextrins (DPw 12) was investigated to gain a basic understanding of the interactions of boric acid derivatives with oligo- and polyglucans. By means of MS and NMR experiments, it was possible to show a first stage formation of a six-membered ring at C-4 and C-6 of the non-reducing glucose occurs as in the case of mono-saccharides. If the amount of reagent is increased the formation of seven-membered rings at the secondary OH moieties is observed. Even the existence of two of these large ring-systems in the direct neighborhood was found. Application of an excess of boronation reagent led to dimerization reactions of Me-beta-D-clb via the primary reducing glucose residue as confirmed by DOSY NMR studies. Preliminary C-13 NMR studies for the interaction of cellodextrins with PBA in DMSO solution confirmed a functionalization at the trans-1,2-diol moieties of these oligomers. The amount of reagent applied may either was shown to lead to soluble products or to insoluble cross-linked material. (C) 2009 Elsevier Ltd. All rights reserved.