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 | 157553-87-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• CAS: 157553-87-2
• 化学式: C₇₃H₈₃NO₁₆Si
• 分子量: 1258.54
• InChiKey: BERCKKCHEDHIIE-CEYTZBEBSA-N

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 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
  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