4-acetoxy-2-[7-benzoyloxy-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 | 224035-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-acetoxy-2-[7-benzoyloxy-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
• CAS: 224035-75-0
• 化学式: C₄₅H₅₆F₃NO₁₉Si
• 分子量: 1000.02
• InChiKey: WIXLKQHBZIFSIN-YTAAXGCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  69.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  242.28
• 氢给体数：
  1.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  4-acetoxy-2-[7-benzoyloxy-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 、 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
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 4,6-O-benzylidene-β-D-galactopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 4-acetoxy-2-[7-benzoyloxy-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
  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

• Studies on the sialylation of galactoses with different C-5 modified sialyl donors
  作者：Jianzhi Gong、Han Liu、John M. Nicholls、Xuechen Li

  DOI：10.1016/j.carres.2012.08.007

  日期：2012.11

  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.