2-chloroethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside | 887641-02-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-chloroethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside；(2R,3S,4R,5R,6R)-5-acetamido-2-(acetoxymethyl)-6-(2-chloroethoxy)tetrahydro-2H-pyran-3,4-diyl diacetate；[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-(2-chloroethoxy)oxan-2-yl]methyl acetate
• CAS: 887641-02-3
• 化学式: C₁₆H₂₄ClNO₉
• 分子量: 409.821
• InChiKey: DRVVQXMTZMNEAU-OXGONZEZSA-N

物化性质

• 沸点：
  556.8±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  126.46
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-chloroethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 四丁基碘化铵 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成
  参考文献：
  名称：

  Glycoclusters as lectin inhibitors: comparative analysis on two plant agglutinins with different folding as a step towards rules for selectivity

  摘要：

  The emerging physiological significance of carbohydrate (glycan) protein (lectin) recognition engenders the interest to design synthetic inhibitors with a high level of selectivity among natural sugar receptors. Plant agglutinins are common models to determine structure activity relationships. Focussing on the contribution of valency towards selectivity, copper-catalysed azide (sugar derivative)-alkyne (scaffold) cycloaddition yielded a panel of 10 bi- to tetravalent glycoclusters with N-acetylglucosamine as the bioactive headgroup. They were introduced into assays using (neo)glycoproteins and cell surfaces as platforms to study carbohydrate-dependent lectin binding. The ability of the bivalent compounds, which exhibit a distance profile of the sugar headgroups of about 16-21 angstrom, for intramolecular bridging of two contact sites from the eight hevein domains of wheat germ agglutinin led to comparatively high enhancements of inhibitory potency relative to a tetrameric leguminous lectin (distance profile of 50-70 angstrom between sugar-specific sites), especially for a beta-S-glycoside. The extent of inhibition at fixed concentrations of the sugar depended on the type of matrix used for the assay. Increases to tri- and tetravalency played a less important role than the anomeric position to keep cross-reactivity low, these tested topologies enabling cross-linking for both lectins. The potential for cis-interactions (intramolecular interactions), with glycoclusters serving as molecular rulers, is suggested to help designing selective blocking reagents. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.07.020
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-trifluoroacetamido-α-D-glucopyranosyl chloride 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 2-chloroethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of defined mono-de-N-acetylated β-(1→6)-N-acetyl-d-glucosamine oligosaccharides to characterize PgaB hydrolase activity

  摘要：

  使用汇合合成法得到了单乙酰化的β-(1→6)-N-乙酰-D-葡萄糖胺五糖和七糖。去乙酰化的位置决定了PgaB水解的选择性。

  DOI：

  10.1039/c9ob02079a

文献信息

• Synthesis of oligosaccharides related to the HNK-1 antigen. 5. Synthesis of a sulfo-mimetic of the HNK-1 antigenic trisaccharide
  作者：E. V. Sukhova、A. V. Dubrovskii、Yu. E. Tsvetkov、N. E. Nifantiev

  DOI：10.1007/s11172-007-0258-y

  日期：2007.8

  Abstract2-Aminoethyl 3,6-di-O-sulfo-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranoside, which is the sulfo-mimetic of the antigenic trisaccharide HNK-1, and the corresponding monosulfates, viz., 2-aminoethyl 3-O-sulfo-and 2-aminoethyl 6-O-sulfo-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→ 4)-2-acetamido-2-deoxy-β-D-glucopyranosides, were synthesized. 2-Azidoethyl

  摘要2-氨基乙基3,6-二-O-磺基-β-D-吡喃葡萄糖基-(1→3)-β-D-吡喃半乳糖基-(1→4)-2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷，它是抗原性三糖 HNK-1 的磺基模拟物，以及相应的单硫酸盐，即 2-氨基乙基 3-O-磺基-和 2-氨基乙基 6-O-磺基-β-D-吡喃葡萄糖基-（1 →3)-β-D-吡喃半乳糖基-(1→4)-2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷被合成。2-叠氮乙基 2,4-二-O-苯甲酰基-β-D-吡喃葡萄糖基-(1→3)-2,4,6-三-O-苯甲酰基-β-D-吡喃半乳糖基-(1→4)-2 -acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glupyranoside 作为硫酸化三糖的常见前体。该化合物是根据 [2+1] 模式从单糖前体合成的：3,6-二-O-乙酰基-2,4-二-O-苯甲酰基-D-吡喃葡萄糖基三氯乙酰亚胺，烯丙基