methyl 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside | 110319-39-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside
• 英文别名: methyl 2,3,4-tri-O-benzoyl-6-O-tert-butyldiphenylsilyl-1-β-D-galactopyranoside；Bz(-2)[Bz(-3)][Bz(-4)][TBDPS(-6)]b-Gal1Me；[(2R,3S,4S,5R,6R)-4,5-dibenzoyloxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-6-methoxyoxan-3-yl] benzoate
• CAS: 110319-39-6
• 化学式: C₄₄H₄₄O₉Si
• 分子量: 744.913
• InChiKey: WUUPISRMPWBNRI-XMDPSZRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  54
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside 在 甲醇 、 乙酰氯 作用下， 以 乙醚 为溶剂， 以88%的产率得到methyl 2,3,4-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Selective silylation of .beta.-D-galactosides. A new approach to the synthesis of (1 .fwdarw. 6)-.beta.-D-galactopyranooligosaccharides

  摘要：

  DOI：

  10.1021/jo00232a036
• 作为产物：
  描述：

  甲基-Β-D-吡喃半乳糖苷 在 2,4,6-三甲基吡啶 、 4-二甲氨基吡啶 、 silver nitrate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 methyl 2,3,4-tri-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Selective silylation of .beta.-D-galactosides. A new approach to the synthesis of (1 .fwdarw. 6)-.beta.-D-galactopyranooligosaccharides

  摘要：

  DOI：

  10.1021/jo00232a036

文献信息

• Coupling reactions of O-(trimethylsilyl) glycosides and 6-O-(tert-butyldiphenylsilyl)-protected galactosides in the presence of trimethylsilyl triflate. A new method of forming .beta.-(1 .fwdarw. 6)-oligosaccharidic linkages
  作者：Eugenia M. Nashed、Cornelis P. J. Glaudemans

  DOI：10.1021/jo00287a026

  日期：1989.12
• NASHED, EUGENIA M.;GLAUDEMANS, CORNELIS P. J., J. ORG. CHEM., 54,(1989) N6, C. 6116-6118
  作者：NASHED, EUGENIA M.、GLAUDEMANS, CORNELIS P. J.

  DOI：——

  日期：——
• NASHED, EUGENIA M.;GLAUDEMANS, CORNELIS P. J., J. ORG. CHEM., 52,(1987) N 23, 5255-5260
  作者：NASHED, EUGENIA M.、GLAUDEMANS, CORNELIS P. J.

  DOI：——

  日期：——
• Synthesis of specifically deoxygenated ligands related to (1→6)-β-d-galacto-oligosaccharides, and studies on their binding to monoclonal antigalactan antibodies
  作者：Thomas Ziegler、Viliam Pavliak、Tsu-Hsing Lin、Pavol Kováč、Cornelis P.J. Glaudemans

  DOI：10.1016/0008-6215(90)84033-q

  日期：1990.9

  Synthetic deoxygenated derivatives of methyl beta-glycosides of (1----6)-beta-D-galacto-oligosaccharides were prepared, and their binding to antigalactan monoclonal antibodies X24 and J539 (Fab') was studied. The results suggest the involvement of an additional, critical hydrogen bond in the highest affinity subsite (A), which now appears to require two hydrogen bonds from the 2- and 3-hydroxyls of the galactosyl residue to the protein, and one from the protein to O-4 of that residue. The data obtained with a series of oligosaccharides deoxygenated at position 3(1), 3(2), 3(3), 4(1), 4(2), or 4(3) support the binding patterns and subsite-arrangement inferred previously from studies with large numbers of deoxyfluoro-substituted ligands and this family of antibodies.
• Selective silylation of .beta.-D-galactosides. A new approach to the synthesis of (1 .fwdarw. 6)-.beta.-D-galactopyranooligosaccharides
  作者：Eugenia M. Nashed、Cornelis P. J. Glaudemans

  DOI：10.1021/jo00232a036

  日期：1987.11