2-(trimethylsilyl)ethyl 4-O-<3-O-(2,4-dideoxy-2-acetamido-β-D-xylo-hexopyranosyl)-α-D-galactopyranosyl>-β-D-galactopyranoside | 157553-88-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 4-O-<3-O-(2,4-dideoxy-2-acetamido-β-D-xylo-hexopyranosyl)-α-D-galactopyranosyl>-β-D-galactopyranoside
• 英文别名: N-[(2S,3R,4S,6S)-2-[(2R,3R,4S,5S,6R)-2-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-(2-trimethylsilylethoxy)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 157553-88-3
• 化学式: C₂₅H₄₇NO₁₅Si
• 分子量: 629.731
• InChiKey: LHURVCCUERLMNJ-MVVXCQEASA-N

物化性质

• 沸点：
  903.0±65.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.04
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  246
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-<2,4,6-tri-O-benzyl-3-O-(2,4-dideoxy-2-phthalimido-β-D-xylo-hexopyranosyl)-α-D-galactopyranosyl>-β-D-galactopyranoside 在 palladium on activated charcoal 氢气 、 一水合肼 作用下， 以 甲醇 、 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 4.5h， 生成 2-(trimethylsilyl)ethyl 4-O-<3-O-(2,4-dideoxy-2-acetamido-β-D-xylo-hexopyranosyl)-α-D-galactopyranosyl>-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of the 2''-Hydroxy, 4''-Deoxy and 4''-Epi Analogues of beta-D-GalNAc-(1->3)-alpha-D-Gal-(1->4)-beta-D-Gal, the Terminal Trisaccharide of Globotetraose.

  摘要：

  Radical deoxygenation of methyl 3,6-di-O-benzoyl-2-deoxy-4-0-imidazol-1-yl-thiocarbonyloxy-2-phthalimido-beta-D-glucopyranoside 5 gave methyl 3,6-di-O-benzoyl-2,4-dideoxy-2-phthalimido-beta-D-glucopyranoside 6, which was converted into the corresponding methyl thioglycoside donor 9. Methylsulfenyl trifluoromethane-sulfonate-promoted glycosylation of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-alpha-D-galactopyranosyl)-beta-D-galactopyranoside 10, followed by removal of protecting groups gave the 4''-deoxy analogue 12 of the terminal trisaccharide of globotetraose. Silver trifluoromethanesulfonate-promoted glycosylation of the same disaccharide alcohol 10 with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-alpha/beta-D-glucopyranosyl bromide 13 and 2.3,4,6-tetra-0-acetyl-alpha-D-galactopyranosyl bromide 16, followed by deblocking, gave the 2''-hydroxy and 4''-epi analogues 15 and 18. respectively.

  DOI：

  10.3891/acta.chem.scand.48-0356

文献信息

• Synthesis of the 2''-Hydroxy, 4''-Deoxy and 4''-Epi Analogues of beta-D-GalNAc-(1-&gt;3)-alpha-D-Gal-(1-&gt;4)-beta-D-Gal, the Terminal Trisaccharide of Globotetraose.
  作者：Ulf Nilsson、Anikó Wendler、Göran Magnusson、Man Shun Soon Huang、Thorleif Anthonsen、Hari N. Pati、Kirpal S. Bisht、Virinder S. Parmar、George W. Francis

  DOI：10.3891/acta.chem.scand.48-0356

  日期：——

  Radical deoxygenation of methyl 3,6-di-O-benzoyl-2-deoxy-4-0-imidazol-1-yl-thiocarbonyloxy-2-phthalimido-beta-D-glucopyranoside 5 gave methyl 3,6-di-O-benzoyl-2,4-dideoxy-2-phthalimido-beta-D-glucopyranoside 6, which was converted into the corresponding methyl thioglycoside donor 9. Methylsulfenyl trifluoromethane-sulfonate-promoted glycosylation of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-alpha-D-galactopyranosyl)-beta-D-galactopyranoside 10, followed by removal of protecting groups gave the 4''-deoxy analogue 12 of the terminal trisaccharide of globotetraose. Silver trifluoromethanesulfonate-promoted glycosylation of the same disaccharide alcohol 10 with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-alpha/beta-D-glucopyranosyl bromide 13 and 2.3,4,6-tetra-0-acetyl-alpha-D-galactopyranosyl bromide 16, followed by deblocking, gave the 2''-hydroxy and 4''-epi analogues 15 and 18. respectively.