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 | 224035-66-9

• 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-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
• CAS: 224035-66-9
• 化学式: C₃₈H₅₂F₃NO₁₈Si
• 分子量: 895.907
• InChiKey: NZPUERRLWRDPLM-GUUAVNFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  61.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  236.21
• 氢给体数：
  2.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  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 、 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
  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 、 methyl [phenyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-D-galacto-non-2-ulopyranosid]onate 在 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， 以61%的产率得到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
  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 selectin-binding activity of N-deacetylsialyl Lewis X ganglioside
  作者：Masanori Yamaguchi、Hideharu Ishida、Christine Galustian、Ten Feizi、Makoto Kiso

  DOI：10.1016/s0008-6215(02)00274-4

  日期：2002.11

  reduction of the azido group, N-acylation with octadecanoic acid, and the complete removal of the protecting groups gave the desired N-deacetylsialyl Lewis X ganglioside. L-Selectin bound more strongly to N-deacetylsialyl Lewis X ganglioside than to the sialyl Lewis X ganglioside, whereas E- and P-selectins bound equally well to the two gangliosides.

  合成了唾液酸化的路易斯X神经节苷脂的新型类似物N-去乙酰唾液酸化的路易斯X神经节苷脂。4,7,8,9-四-O-乙酰基-3,5-二脱氧-5-三氟乙酰胺基-D-甘油-α-D-半乳糖-2-壬基吡喃二磺酸甲酯-（2-> 3）-2,4 ，6-三-O-苯甲酰基-D-吡喃半乳糖基三氯乙酰亚胺酸酯与2-（三甲基甲硅烷基）乙基[2-乙酰氨基-6-O-苄基-2-脱氧-3-O-（4-甲氧基苄基）-β-D偶联-吡喃葡萄糖基]-（1-> 3）-[2,4,6-三-O-苄基-β-D-吡喃半乳糖基]-（1-> 4）-2,3,6-三-O-苄基-β-D-吡喃半乳糖苷以高收率得到所需的五糖。以N-碘代琥珀酰亚胺-三氟甲烷磺酸为促进剂，通过除去3-甲氧基苄基而衍生自其前体的五糖受体的糖基化与L-岩藻糖的苯基1-硫代糖苷衍生物进行糖基化。适当操作六糖的保护基团可得到相应的亚氨基糖基亚氨酸酯，其与（2S，3R，4E）-2-叠氮基-3