(methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-4,6-di-O-acetyl-2-O-benzoyl-D-galactopyranosyl trichloroacetimidate | 224035-67-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-4,6-di-O-acetyl-2-O-benzoyl-D-galactopyranosyl trichloroacetimidate
• CAS: 224035-67-0
• 化学式: C₃₉H₄₄Cl₃F₃N₂O₂₁
• 分子量: 1040.13
• InChiKey: SLUMGPQLLMRWCK-YILKTDICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  68.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  300.27
• 氢给体数：
  2.0
• 氢受体数：
  22.0

反应信息

• 作为反应物：
  描述：

  (methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-4,6-di-O-acetyl-2-O-benzoyl-D-galactopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium methylate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 132.0h， 生成 cyclic sialyl GM4
  参考文献：
  名称：

  Synthesis of novel ganglioside GM4 analogues containing N-deacetylated and lactamized sialic acid: probes for searching new ligand structures for human L-selectin

  摘要：

  Novel ganglioside GM4 analogues, which contain N-deacetylated or lactamized sialic acid instead of usual N-acetylneuraminic acid, were synthesized in a highly efficient manner. (Methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero alpha -D-galacto-2-nonulopyranosylonate)-(2-->3)-4,6-di-O-acetyl-2-O-benzoyl-D-galactopyranosyl trichloroacetimidate was coupled with 2-(tetradecyl)hexadecanol to give the desired beta -glycoside in high yield. Successive O- and N-deacylation, and saponification of the methyl ester group afforded the N-deacetylated sialyl derivative that was converted by treatment with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in Me2SO into the lactamized sialic acid-containing ganglioside GM4 analogue. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00278-0
• 作为产物：
  描述：

  4-acetoxy-2-[7-hydroxy-2-phenyl-6-(2-trimethylsilanyl-ethoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-6-(1,2,3-triacetoxy-propyl)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢气 、 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 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 (methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->3)-4,6-di-O-acetyl-2-O-benzoyl-D-galactopyranosyl trichloroacetimidate
  参考文献：
  名称：

  The First Total Synthesis of 6-Sulfo-de-N-acetylsialyl Lewisx Ganglioside: A Superior Ligand for Human L-Selectin

  摘要：

  Originally discovered as a minor by-product of 6-sulfo-N-acetylsialyl Lewis(x) , the de-N-acetylated form 1 is a superior L-selectin ligand to the N-acetyl form. To substantiate the extraordinary reactivity of 1, it was synthesized for the first time and its binding to L-selectin investigated. Compound 1 and related structures may be high-affinity endogenous ligands for L-selectin that are involved in the interaction of leukocytes with the vascular endothelium.

  DOI：

  10.1002/(sici)1521-3773(19990419)38:8<1131::aid-anie1131>3.0.co;2-b

文献信息

• Differential Receptor Binding Affinities of Influenza Hemagglutinins on Glycan Arrays
  作者：Hsin-Yu Liao、Che-Hsiung Hsu、Shih-Chi Wang、Chi-Hui Liang、Hsin-Yung Yen、Ching-Yao Su、Chien-Hung Chen、Jia-Tsrong Jan、Chien-Tai Ren、Chung-Hsuan Chen、Ting-Jen R. Cheng、Chung-Yi Wu、Chi-Huey Wong

  DOI：10.1021/ja104657b

  日期：2010.10.27

  A library of 27 sialosides, including seventeen 2,3-linked and ten 2,6-linked glycans, has been prepared to construct a glycan array and used to profile the binding specificity of different influenza hemagglutinins (HA) subtypes, especially from the 2009 swine-originated H1N1 and seasonal influenza viruses. It was found that the HAs from the 2009 H1N1 and the seasonal Brisbane strain share similar binding profiles yet different binding affinities toward various alpha 2,6 sialosides. Analysis of the binding profiles of different HA subtypes indicate that a minimum set of 5 oligosaccharides can be used to differentiate influenza H1, H3, H5, H7, and H9 subtypes. In addition, the glycan array was used to profile the binding pattern of different influenza viruses. It was found that most binding patterns of viruses and HA proteins are similar and that glycosylation at Asn27 is essential for receptor binding.