3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl trichloroacetimidate | 1064679-24-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl trichloroacetimidate
• 英文别名: [(2R,3S,4S,5R,6S)-3-acetyloxy-5-benzoyloxy-4-[(2S,3R,4R,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-(1,3-dioxoisoindol-2-yl)oxan-2-yl]oxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl benzoate
• CAS: 1064679-24-8
• 化学式: C₄₄H₄₁Cl₃N₂O₁₈
• 分子量: 992.171
• InChiKey: ZWBUHPMLIMKZBV-IIQDBQSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  67
• 可旋转键数：
  21
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  256
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl trichloroacetimidate 、 4-methoxyphenyl (6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以84%的产率得到[(2R,3S,4S,5R,6S)-3-acetyloxy-6-[(2R,3S,4R,5R,6S)-6-[(2S,3R,4S,5S,6R)-5-acetyloxy-2-[(2R,3R,4S,5R,6S)-6-(4-methoxyphenoxy)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-3-phenylmethoxy-6-(phenylmethoxymethyl)oxan-4-yl]oxy-5-(1,3-dioxoisoindol-2-yl)-4-hydroxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-benzoyloxy-4-[(2S,3R,4R,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-(1,3-dioxoisoindol-2-yl)oxan-2-yl]oxyoxan-2-yl]methyl benzoate
  参考文献：
  名称：

  Concise synthesis of two pentasaccharides corresponding to the α-chain oligosaccharides of Neisseria gonorrhoeae and Neisseria meningitidis

  摘要：

  Two pentasaccharides containing a common tetrasaccharide (lacto-N-neotetraose) core, and D-galactosamine and N-acetyl neuraminic acid in the non-reducing ends, respectively, corresponding to the lipooligosaccharides of Neisseria gonorrhoeae and Neisseria meningitidis were synthesized in a very concise manner from a common trisaccharide derivative using minimum number of steps. Thioglycosides and glycosyl trichloroacetimidate have been used as glycosyl donors for glycosylations and yields were excellent in every step. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.004
• 作为产物：
  描述：

  4-methoxyphenyl (3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl)-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranoside 、 三氯乙腈 在 ammonium cerium(IV) nitrate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 水 、 乙腈 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Concise synthesis of two pentasaccharides corresponding to the α-chain oligosaccharides of Neisseria gonorrhoeae and Neisseria meningitidis

  摘要：

  Two pentasaccharides containing a common tetrasaccharide (lacto-N-neotetraose) core, and D-galactosamine and N-acetyl neuraminic acid in the non-reducing ends, respectively, corresponding to the lipooligosaccharides of Neisseria gonorrhoeae and Neisseria meningitidis were synthesized in a very concise manner from a common trisaccharide derivative using minimum number of steps. Thioglycosides and glycosyl trichloroacetimidate have been used as glycosyl donors for glycosylations and yields were excellent in every step. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.07.004