2-(trimethylsilyl)ethyl (methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-(2→3)-4,6-di-O-acetyl-2-O-benzoyl-β-D-galacotopyranoside | 342897-41-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl (methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-(2→3)-4,6-di-O-acetyl-2-O-benzoyl-β-D-galacotopyranoside
• CAS: 342897-41-0
• 化学式: C₄₂H₅₆F₃NO₂₁Si
• 分子量: 995.981
• InChiKey: FRIGNLDQQWXOMH-FDEZXBCSSA-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：
  20.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  276.42
• 氢给体数：
  1.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl (methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-(2→3)-4,6-di-O-acetyl-2-O-benzoyl-β-D-galacotopyranoside 在 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2,2,2-Trichloroacetimidate (methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-(2→3)-4,6-di-O-acetyl-2-O-benzoyl-α-D-galacotopyranoside
  参考文献：
  名称：

  Studies on the sialylation of galactoses with different C-5 modified sialyl donors

  摘要：

  Synthetic sialylated glycans provide useful tools to study carbohydrate-mediated biological recognition; however chemical sialylation is the most challenging practice in preparative carbohydrate chemistry, which is often associated with low yields and poor stereoselectivity. Herein, we conducted extensive studies on sialylation with five types of 5-N-modified sialyl donors and four types of galactosyl acceptors. Our studies have shown that a good combination between the donor and the acceptor seems necessary to achieve high yield and stereoselectivity. None of the donors or acceptors showed 'universal' utility toward the sialylation reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.08.007
• 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 作用下， 以 溶剂黄146 为溶剂， 生成 2-(trimethylsilyl)ethyl (methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-(2→3)-4,6-di-O-acetyl-2-O-benzoyl-β-D-galacotopyranoside
  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