3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-galactopyranosyl trichloroacetimidate | 401900-32-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-galactopyranosyl trichloroacetimidate
• 英文别名: Bn(-2)Gal3Ac4Ac6Ac(b1-6)Gal2Ac3Ac4Ac(b)-O-C(NH)CCl3；[(2R,3S,4S,5R,6R)-3,4-diacetyloxy-5-phenylmethoxy-6-[[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 401900-32-1
• 化学式: C₃₃H₄₀Cl₃NO₁₇
• 分子量: 829.036
• InChiKey: VGZXAPMUWPVZEH-VBEVKOTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  54
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  228
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-galactopyranosyl trichloroacetimidate 在 palladium on activated charcoal 三氟甲磺酸三甲基硅酯 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 14.0h， 生成 3,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-galactopyranosyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Synthesis of the α-l-Araf-(1→2)-β-d-Galp-(1→6)-β-d-Galp-(1→6)-[α-l-Araf-(1→2)]-β-d-Galp-(1→6)-d-Gal hexasaccharide as a possible repeating unit of the cell-cultured exudates of Echinacea purpurea arabinogalactan

  摘要：

  For the characterization of the supposed epitope of an arabinogalactan, isolated from the extract of the cell-cultured Echinacea purpurea. the title hexasaccharide was synthesized. The whole synthetic route was based on the 6-O-(methoxydimethyl)methyl ether (MIP) protecting group strategy. 2-O-Benzyl-3,4-O-isopropylidene-6-O-(methoxydimethyl)methyl-beta -D-galactopyranosyl-(1 --> 6)-1,2:3.4-di-O-isopropylidene-alpha -D-galactopyranose was used to prepare the desired glycosyl donor and glycosyl acceptor both carrying a persistent O-benzyl group at position 2'. Reaction of the digalactose donor and the digalactose acceptor resulted in a beta-(1 --> 6)-linked galactose-containing tetrasaccharide in which OH-2' and OH-2'" were substituted with benzyl groups. Hydrogenolytic removal of the benzyl groups of the tetragalactose compound gave the diol aglycon which was diarabinosylated in one step to furnish the protected target compound, whose deprotection led to the title hexasaccharide. All of the synthesized compounds were characterized by H-1 and C-13 NMR spectra, as well as by MALDI-TOF mass-spectrometry measurements. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00232-4
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl-(1->6)-1,2,3,4-tetra-O-acetyl-α-D-galactopyranose 在 乙酸肼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.5h， 生成 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-acetyl-β-D-galactopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of the α-l-Araf-(1→2)-β-d-Galp-(1→6)-β-d-Galp-(1→6)-[α-l-Araf-(1→2)]-β-d-Galp-(1→6)-d-Gal hexasaccharide as a possible repeating unit of the cell-cultured exudates of Echinacea purpurea arabinogalactan

  摘要：

  For the characterization of the supposed epitope of an arabinogalactan, isolated from the extract of the cell-cultured Echinacea purpurea. the title hexasaccharide was synthesized. The whole synthetic route was based on the 6-O-(methoxydimethyl)methyl ether (MIP) protecting group strategy. 2-O-Benzyl-3,4-O-isopropylidene-6-O-(methoxydimethyl)methyl-beta -D-galactopyranosyl-(1 --> 6)-1,2:3.4-di-O-isopropylidene-alpha -D-galactopyranose was used to prepare the desired glycosyl donor and glycosyl acceptor both carrying a persistent O-benzyl group at position 2'. Reaction of the digalactose donor and the digalactose acceptor resulted in a beta-(1 --> 6)-linked galactose-containing tetrasaccharide in which OH-2' and OH-2'" were substituted with benzyl groups. Hydrogenolytic removal of the benzyl groups of the tetragalactose compound gave the diol aglycon which was diarabinosylated in one step to furnish the protected target compound, whose deprotection led to the title hexasaccharide. All of the synthesized compounds were characterized by H-1 and C-13 NMR spectra, as well as by MALDI-TOF mass-spectrometry measurements. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00232-4