p-methoxyphenyl 2,3-di-O-benzoyl-6-O-tert-butyldimethylsilyl-4-O-(2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranosyl)-β-D-glucopyranoside | 848863-40-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 2,3-di-O-benzoyl-6-O-tert-butyldimethylsilyl-4-O-(2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranosyl)-β-D-glucopyranoside
• 英文别名: [(2R,4aR,6R,7R,8S,8aR)-7-benzoyloxy-6-[(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-(4-methoxyphenoxy)oxan-3-yl]oxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] benzoate
• CAS: 848863-40-1
• 化学式: C₆₀H₆₂O₁₆Si
• 分子量: 1067.23
• InChiKey: SHELECLXKRBHEH-DMMKXPKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.95
• 重原子数：
  77
• 可旋转键数：
  22
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  179
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 2,3-di-O-benzoyl-6-O-tert-butyldimethylsilyl-4-O-(2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranosyl)-β-D-glucopyranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以70%的产率得到p-methoxyphenyl 2,3-di-O-benzoyl-4-O-(2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Exploiting an aromatic aglycone as a reporter of glycosylation stereochemistry in the synthesis of 1,6-linked maltooligosaccharides

  摘要：

  Analysis of glycosylation stercoselectivity in the synthesis of branched maltooligosaccharides is hampered by poor spectral dispersion due to the repetitive nature of the saccharide chain and overlap of sugar H-l signals with benzylic proton signals from the typically used benzyl ether protecting groups. A suitably protected p-methoxyphenyl maltoside acceptor, when coupled with benzylated maltooligosaccharide donors, gives discrete aglycone H-1 NMR signals that can be used to report on the stereo selectivity of 1,6-glycosylation reactions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.047
• 作为产物：
  描述：

  p-methoxyphenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside 在 吡啶 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 p-methoxyphenyl 2,3-di-O-benzoyl-6-O-tert-butyldimethylsilyl-4-O-(2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Exploiting an aromatic aglycone as a reporter of glycosylation stereochemistry in the synthesis of 1,6-linked maltooligosaccharides

  摘要：

  Analysis of glycosylation stercoselectivity in the synthesis of branched maltooligosaccharides is hampered by poor spectral dispersion due to the repetitive nature of the saccharide chain and overlap of sugar H-l signals with benzylic proton signals from the typically used benzyl ether protecting groups. A suitably protected p-methoxyphenyl maltoside acceptor, when coupled with benzylated maltooligosaccharide donors, gives discrete aglycone H-1 NMR signals that can be used to report on the stereo selectivity of 1,6-glycosylation reactions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.047

文献信息

• Exploiting an aromatic aglycone as a reporter of glycosylation stereochemistry in the synthesis of 1,6-linked maltooligosaccharides
  作者：Laurence Marmuse、Sergey A. Nepogodiev、Robert A. Field

  DOI：10.1016/j.tetasy.2004.11.047

  日期：2005.1

  Analysis of glycosylation stercoselectivity in the synthesis of branched maltooligosaccharides is hampered by poor spectral dispersion due to the repetitive nature of the saccharide chain and overlap of sugar H-l signals with benzylic proton signals from the typically used benzyl ether protecting groups. A suitably protected p-methoxyphenyl maltoside acceptor, when coupled with benzylated maltooligosaccharide donors, gives discrete aglycone H-1 NMR signals that can be used to report on the stereo selectivity of 1,6-glycosylation reactions. (C) 2004 Elsevier Ltd. All rights reserved.