[(5aR,6R,8R,9S,9aR)-6-methoxy-2,4-diphenyl-9-[[(1S,2S,7R,9S,10R)-4,12,14-triphenyl-3,5,8,11,13,15-hexaoxa-4,12,14-triboratricyclo[8.5.0.02,7]pentadecan-9-yl]oxy]-6,8,9,9a-tetrahydro-5aH-pyrano[3,4-f][1,3,5,2,4]trioxadiborepin-8-yl]methanol | 1213789-33-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(5aR,6R,8R,9S,9aR)-6-methoxy-2,4-diphenyl-9-[[(1S,2S,7R,9S,10R)-4,12,14-triphenyl-3,5,8,11,13,15-hexaoxa-4,12,14-triboratricyclo[8.5.0.02,7]pentadecan-9-yl]oxy]-6,8,9,9a-tetrahydro-5aH-pyrano[3,4-f][1,3,5,2,4]trioxadiborepin-8-yl]methanol
• CAS: 1213789-33-3
• 化学式: C₄₃H₄₃B₅O₁₃
• 分子量: 821.862
• InChiKey: FEPGALROFFLIAG-GNGAXZRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.45
• 重原子数：
  61
• 可旋转键数：
  9
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  131
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  苯硼酸酐 、 甲基 4-O-beta-D-吡喃葡萄糖基-beta-D-吡喃葡萄糖苷 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 [(5aR,6R,8R,9S,9aR)-6-methoxy-2,4-diphenyl-9-[[(1S,2S,7R,9S,10R)-4,12,14-triphenyl-3,5,8,11,13,15-hexaoxa-4,12,14-triboratricyclo[8.5.0.02,7]pentadecan-9-yl]oxy]-6,8,9,9a-tetrahydro-5aH-pyrano[3,4-f][1,3,5,2,4]trioxadiborepin-8-yl]methanol 、
  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.