2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate | 231616-43-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Gal(b1-6)[Bz(-2)][Bz(-3)][Bz(-4)]Gal(a)-O-C(NH)CCl3；[(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[[(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methoxy]oxan-2-yl]methyl benzoate
• CAS: 231616-43-6
• 化学式: C₆₃H₅₀Cl₃NO₁₈
• 分子量: 1215.44
• InChiKey: VQXGIRIBXXZASZ-RRMYCOOVSA-N

物化性质

• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  85
• 可旋转键数：
  27
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  245
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 、 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到
  参考文献：
  名称：

  存在于白术DC的根茎中的β-（1→6）支链β-（1→3）相连的d-半乳聚糖的合成

  摘要：

  摘要用2,3,4,6-四-O-苯甲酰基-α-d-吡喃半乳糖基三氯乙酰亚氨酸酯（1 ），4-甲氧基苯基2,3,4-三-O-苯甲酰基-β-d-吡喃半乳糖苷（2），6-O-乙酰基-2,3,4-三-O-苯甲酰基-α-d-吡喃半乳糖基三氯乙酰亚氨酸（5），4-甲氧基苯基6-O-乙酰基-2,4-二-O-苯甲酰基-β-d-吡喃半乳糖苷（22）和4-甲氧基苯基2,4,6-三-O-苯甲酰基-β- d-半乳糖吡喃糖苷（26）为关键合成子。将2与1偶联，然后将1-OMP氧化裂解，随后形成三氯乙酰亚氨酸酯，得到β-（1→6）连接的二糖供体4。2与5的缩合以及随后的甲醇解选择性脱乙酰基产生了β-（1→6）连接的二糖受体7。7与4的反应，1-OMP的氧化裂解和三氯乙亚氨酸盐的生成产生了四糖供体9。相似地合成五（15），六（17）和七糖供体19。同时，用22处理1产生β-（1→3）-连接的二糖23和α-（1→3）-连接

  DOI：

  10.1016/j.carres.2005.05.017
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl-6-O-(tert-butyldimethylsilyl)-β-D-galactopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthetic studies on glycosphingolipids from the parasite Echinococcus multilocularis

  摘要：

  Novel neutral glycosphingolipids isolated from the metacestodes of Echinococcus multilocularis by Persat, may be expected to be involved in host-parasite interactions. We have synthesized these glycosphingolipid analogues containing 2-branched fatty alkyl residues in place of ceramide. The glycosylation of galactosyl donors 4 and 5 with each of the accepters 2 and 11 in the presence of N-iodosuccinimide (NIS)/TfOH, and the glycosylation of fucosyl donor 13 with accepters 12 and 20 in the presence of dimethyl(methylthio)sulfonium triflate (DMTST) gave the desired oligosaccharide derivatives at good yield. The fully per-O-acylated 2-(trimethylsilyl)ethyl glycosides 6, 15, 21, and 26 were converted to glycosylimidates 7, 16, 22, and 27, which were condensed with 2-(tetradecyl)hexadecanol and subsequently deacylated give four target glycosphingolipid analogues. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00027-0

文献信息

• Synthesis of pennogenyl saponin analogs using three methods
  作者：Shouqin Zhang、Jinsong Zhang、Changzheng Wang

  DOI：10.1007/s11172-006-0498-2

  日期：2006.10

  The synthesis of pennogenyl saponins and related compounds using three popular methods of glycosylation has been reported for the first time. Glycosyl halides, glycosyl trichloroacetimidates, and thioglycosides were used as glycosyl donors in the reactions with pennogenin as the glycosyl acceptor. The reactions occur selectively with the C(3)OH group due to the difference in steric accessibility of the hydroxyl groups at the C(3) and C(17) atoms of pennogenin. This makes it possible to synthesize a series of pennogenyl saponins without C(17)OH group protection.

  首次报道了利用三种常见糖基化方法合成 pennogenyl 皂苷及相关化合物的情况。在以 pennogenin 为糖基受体的反应中，采用了糖基卤化物、糖基三氯乙酰亚胺酯和硫代糖苷作为糖基供体。反应由于 pennogenin 的 C(3) 和 C(17) 原子上羟基的空间可及性差异，选择性地发生在 C(3)OH 基团上。这使得合成一系列不含 C(17)OH 保护基团的 pennogenyl 皂苷成为可能。
• Synthesis of pennogenyl saponins using three methods
  作者：S. Q. Zhang、J. S. Zhang、C. Z. Wang

  DOI：10.1007/s10600-007-0153-7

  日期：2007.7

  The synthesis of pennogenyl saponins using three important methods of glycosylation is reported in this article. Six correlative compounds (7–12) were first synthesized. As donors (1–6), glycosyl halide, trichloroimidate, and thioglycoside were chosen to study their reaction with the acceptor pennogenin. In these reactions the difference in steric hindrance between 3-OH and 17-OH of pennogenin was utilized skillfully and only the 3-hydroxyl group of pennogenin could be connected with each kind of donors selectively. There was no reaction at the 17-hydroxyl group, which had no protection. The characteristic above makes it convenient to synthesize compounds of pennogenyl saponins.

  本文报道了利用三种重要糖基化方法合成Pennogenyl皂苷。首先合成了6个相关化合物（7-12）。作为供体（1-6），选择了糖基卤化物、三氯咪唑和硫代糖苷与受体Pennogenin反应。在这些反应中巧妙地利用了Pennogenin的3-OH和17-OH之间的立体障碍差异，仅使Pennogenin的3-羟基能够选择性地与每种供体连接。未受保护的17-羟基没有反应。上述特点使得合成Pennogenyl皂苷化合物变得方便。
• One-pot synthesis of a 3,6-branched hexaarabinogalactan using galactopyranosyl thioglycoside diol as a key glycosylating agent
  作者：Hong Huang、Lu Han、Yu-Mei Lan、Ling-Li Zhang

  DOI：10.1080/10286020.2014.917084

  日期：2014.6.3

  We present in this paper the efficient four-component one-pot synthesis of a fully protected hexaarabinogalactan 2 with di-branched structure by using D-thiogalactopyranoside 3,6-diol 3 as the central glycosylating agent. After global deprotection, 2 was converted into the 3-aminopropyl linker-containing free oligosaccharide 1 that is structurally related to ALR-5IIa-1-1, an arabino-3,6-galactan with intestinal immune system modulating activity.