4-hydroxy-(Z)-but-2-enyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside | 324532-87-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-(Z)-but-2-enyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[(Z)-4-hydroxybut-2-enoxy]oxan-2-yl]methyl acetate
• CAS: 324532-87-8
• 化学式: C₁₈H₂₇NO₁₀
• 分子量: 417.413
• InChiKey: YCDRTVXSRJKUDJ-OXITYTPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-hydroxy-(Z)-but-2-enyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 在 二甲基十二/十四烷基叔胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以100%的产率得到4-hydroxy-(Z)-but-2-enyl 2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Probing multivalent carbohydrate–lectin interactions by an enzyme-linked lectin assay employing covalently immobilized carbohydrates

  摘要：

  We report here the synthesis of a series of mono-to trivalent N-acetylglucosamine (GlcNAc) derivatives as ligands for the plant lectin wheat germ agglutinin (WGA). Their WGA binding potencies were determined by an established enzyme-linked lectin assay (ELLA) employing microtiter plates with non-covalently immobilized porcine stomach mucin (PSM) as reference ligand and an ELLA with a new GlcNAc derivative covalently immobilized via a thiourea linkage. Comparison of both assays revealed that the type of presentation of GlcNAc residues on the microtiter plates either as part of a glycoprotein or as a covalently immobilized monosaccharide derivative strongly influences the outcome of the assay. Although the apparent dissociation constants K-D(ELLA) D for the interaction of peroxidase-labeled WGA with the microtiter plates are comparable for both surfaces, IC50 values obtained with the PSM-free ELLA were substantially lower. Even more strikingly, this ELLA displayed a better differentiation between ligands of different valency leading to significantly higher relative inhibitory potencies of multivalent ligands compared to monovalent. Additionally, problems associated with the use of PSM, such as maximum inhibition at considerably less than 100% and poor reproducibility of IC50 values could be overcome with this type of ELLA. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.063
• 作为产物：
  描述：

  ethyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 在 吡啶 、 氟化氢吡啶 、 溶剂黄146 、 三氟甲烷磺酸甲酯 、 锌 作用下， 以 二氯甲烷 为溶剂， 生成 4-hydroxy-(Z)-but-2-enyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Combinatorial Solid-Phase Synthesis of Multivalent Cyclic Neoglycopeptides

  摘要：

  DOI：

  10.1002/1521-3773(20001201)39:23<4348::aid-anie4348>3.0.co;2-x

文献信息

• Copper(II)‐Mediated Activation of Sugar Oxazolines: Mild and Efficient Synthesis of β‐Glycosides of <i>N</i> ‐Acetylglucosamine
  作者：Valentin Wittmann、Dirk Lennartz

  DOI：10.1002/1099-0690(200204)2002:8<1363::aid-ejoc1363>3.0.co;2-#

  日期：2002.4

  2-Methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)[2,1-d]-2-oxazoline (5) was reacted with glycosyl acceptors bearing primary (6, 8, 10, 20) or secondary hydroxy groups (12, 14, 16, 18) in the presence of anhydrous cupric bromide or cupric chloride at elevated temperature to provide 2-acetamido-2-deoxy-β-D-glucopyranosides in 36−92% yield. The reaction conditions are milder than those previously

  使2-甲基-（3,4,6-三-O-乙酰基-1,2-二脱氧-α-D-吡喃吡喃）[2,1 - d ] -2-恶唑啉（5）与带有伯基的糖基受体反应（6，8，10，20）或仲羟基基团（12，14，16，18）在无水溴化铜或氯化铜的存在下，在升高的温度，以提供2-乙酰氨基-2-脱氧-3-β-D-吡喃葡萄糖ef=https://www.molaid.com/MS_187149 target="_blank">吡喃葡萄糖苷收率为36-92％。该反应条件比以前描述的使用p进行恶唑啉活化的条件温和-甲苯磺酸或氯化铁。用三甲基硅烷基叠氮化物（22）和CuCl 2处理恶唑啉可产生2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-β-D-吡喃葡萄糖基叠氮化物（23），产率为69％。（©Wiley-VCH Verlag GmbH，69451 Weinheim，Germany，2002）