4-acetoxy-2-[3-benzoyloxy-5-hydroxy-6-hydroxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-6-(1,2,3-triacetoxy-propyl)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester | 342897-42-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-acetoxy-2-[3-benzoyloxy-5-hydroxy-6-hydroxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-6-(1,2,3-triacetoxy-propyl)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 342897-42-1
• 化学式: C₃₈H₅₂F₃NO₁₉Si
• 分子量: 911.907
• InChiKey: BZDVGXVNULVFDT-VTHJCCHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  62.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  264.28
• 氢给体数：
  3.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  4-acetoxy-2-[3-benzoyloxy-5-hydroxy-6-hydroxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-6-(1,2,3-triacetoxy-propyl)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成
  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：

  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 4-acetoxy-2-[3-benzoyloxy-5-hydroxy-6-hydroxymethyl-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-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

• Synthesis and Antigenic Property of a Novel Sialyl 6‐<i>O</i>‐Sulfo Lewis X Neo‐glycolipid Containing Lactamized Neuraminic Acid
  作者：Masanori Yamaguchi、Hideharu Ishida、Akiko Kanamori、Reiji Kannagi、Makoto Kiso

  DOI：10.1081/car-200030039

  日期：2004.12.29

  Removal of all the acyl protecting groups and subsequent lactamization afforded the lactamized sLex derivative(10), which was converted to the target compound (14) by selective removal of the 4‐methoxyphenyl group and 6‐O‐sulfation of the GlcNAc residue, and removal of all protective groups under the basic conditions furnished the target molecule. The antigenic property of the synthesized neo‐glycolipid

  摘要描述了一种新型的含内酰胺化神经氨酸的6-O-硫酸化sLex新糖脂的合成和抗原特性。甲基（4,7,8,9-四-O-乙酰基-3,5-二甲氧基-5-三氟乙酰胺基-D-甘油-α-D-半乳糖-2-壬醛基吡喃二磺酸甲酯）-（2→3）-的偶联4,6-二-O-乙酰基-2-O-苯甲酰基-1-硫代-β-D-吡喃半乳糖苷（3）与2-（十四烷基）十六烷基（2,3,4-三-O-苄基-α- L-呋喃果糖基）-（1→3）-2-乙酰氨基-2--2-脱氧-6-O-4-甲氧基苯基-β-D-吡喃葡萄糖苷（7）得到了保护的sLex四糖糖脂（8）。除去所有酰基保护基团并随后进行内酰胺化，得到内酰胺化的sLex衍生物（10），通过选择性除去4-甲氧基苯基和GlcNAc残基的6-O-硫酸化，将其转化为目标化合物（14），并且在碱性条件下除去所有保护基提供了目标分子。通过G159单克隆抗体的TLC免疫染色检查了合成的新糖脂的抗原性。