phenyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside | 212128-08-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Gal(b1-6)[Bz(-2)][Bz(-3)][Bz(-4)]Gal(b)-SPh；[(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[[(2R,3S,4S,5R,6S)-3,4,5-tribenzoyloxy-6-phenylsulfanyloxan-2-yl]methoxy]oxan-2-yl]methyl benzoate
• CAS: 212128-08-0
• 化学式: C₆₇H₅₄O₁₇S
• 分子量: 1163.22
• InChiKey: RLRQYCJHVNSYQM-VPXPKCSISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  85
• 可旋转键数：
  27
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  237
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  erythro-N-Palmitoyl-3-O-benzoyl-D-dihydrosphingosin 、 phenyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以43.9%的产率得到2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->1)-(2S,3R)-3-O-benzoyl-2-hexadecanamido-octadecane-1,3-diol
  参考文献：
  名称：

  原生动物门鞘糖脂的合成研究：寄生虫多叶棘球oc糖鞘脂的总合成

  摘要：

  高效和系统的合成的四个中性糖鞘脂已实现从多棘球chin球菌的分离。关键步骤是在N-碘代琥珀酰亚胺（NIS）/ TfOH存在下，使用巯基糖苷与苯甲酰神经酰胺直接对半乳糖基供体进行糖基化反应，从而得到所需的寡糖衍生物。将完全保护的糖苷13、20、22和25脱保护，得到四个目标糖鞘脂（1-4）。

  DOI：

  10.1016/j.carres.2004.09.015
• 作为产物：
  描述：

  苯基-1-硫醇-beta-D-半乳糖苷 在 盐酸 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 Angstroem MS 作用下， 以 吡啶 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 7.08h， 生成 phenyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Scope and Applications of "Active and Latent" Thioglycosyl Donors. Part 4

  摘要：

  The relative reactivity of various thioglycosyl donors having ethyl, phenyl, or parasubstituted phenyl groups with electron donating (N-Ac) or electron withdrawing (NO2) substituents were compared using 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose (3) as standard glycosyl acceptor. The reactivity order was found to decrease from ethyl > phenyl > p-acetamidophenyl > p-nitrophenyl. In the latter situation, when the thioglycosyl donor was also equipped with "disarming" ester protecting groups, they were found to be inert or inactive toward common thiophilic promoters. Alternatively, it was possible to selectively activate the "armed" perbenzylated p-nitrophenyl 1-thio-beta-D-galactopyranoside (21) in the presence of the corresponding "disarmed" perbenzoylated p-nitrophenyl 2,3,4-tri-O-benzoyl-1-thio-beta-D-galactopyranoside (15) which served as the glycosyl acceptor. When both "armed" perbenzylated thioglycosides 7 and 25 were used as thioglycosyl donor and thioglycosyl acceptor, respectively, the milder thiophilic promotor methyl triflate was required for chemoselective activation. These results further demonstrate the potential of "armed and disarmed" "active and latent" thioglycosides in blockwise oligosaccharide syntheses.

  DOI：

  10.1080/07328309808002341

文献信息

• Scope and Applications of "Active and Latent" Thioglycosyl Donors. Part 4
  作者：Suoding Cao、Fernando Hernández-Matéo、René Roy

  DOI：10.1080/07328309808002341

  日期：1998.5.1

  The relative reactivity of various thioglycosyl donors having ethyl, phenyl, or parasubstituted phenyl groups with electron donating (N-Ac) or electron withdrawing (NO2) substituents were compared using 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose (3) as standard glycosyl acceptor. The reactivity order was found to decrease from ethyl > phenyl > p-acetamidophenyl > p-nitrophenyl. In the latter situation, when the thioglycosyl donor was also equipped with "disarming" ester protecting groups, they were found to be inert or inactive toward common thiophilic promoters. Alternatively, it was possible to selectively activate the "armed" perbenzylated p-nitrophenyl 1-thio-beta-D-galactopyranoside (21) in the presence of the corresponding "disarmed" perbenzoylated p-nitrophenyl 2,3,4-tri-O-benzoyl-1-thio-beta-D-galactopyranoside (15) which served as the glycosyl acceptor. When both "armed" perbenzylated thioglycosides 7 and 25 were used as thioglycosyl donor and thioglycosyl acceptor, respectively, the milder thiophilic promotor methyl triflate was required for chemoselective activation. These results further demonstrate the potential of "armed and disarmed" "active and latent" thioglycosides in blockwise oligosaccharide syntheses.
• Synthetic studies on glycosphingolipids from Protostomia phyla: total syntheses of glycosphingolipids from the parasite, Echinococcus multilocularis
  作者：Takeshi Yamamura、Noriyasu Hada、Asuka Kaburaki、Kimiaki Yamano、Tadahiro Takeda

  DOI：10.1016/j.carres.2004.09.015

  日期：2004.12

  neutral glycosphingolipids that have been isolated from the metacestodes of Echinococcus multilocularis have been achieved. A key step is the direct glycosylation of galactosyl donors using thioglycosides with benzoyl ceramide in the presence of N-iodosuccinimide (NIS)/TfOH, which gave the desired oligosaccharide derivatives. The fully protected glycosides 13, 20, 22 and 25 were deprotected to give four

  高效和系统的合成的四个中性糖鞘脂已实现从多棘球chin球菌的分离。关键步骤是在N-碘代琥珀酰亚胺（NIS）/ TfOH存在下，使用巯基糖苷与苯甲酰神经酰胺直接对半乳糖基供体进行糖基化反应，从而得到所需的寡糖衍生物。将完全保护的糖苷13、20、22和25脱保护，得到四个目标糖鞘脂（1-4）。