2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2-deoxy-2-acetamido-3,6-di-O-acetyl-α,β-D-glucopyranose | 68115-84-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2-deoxy-2-acetamido-3,6-di-O-acetyl-α,β-D-glucopyranose
• 英文别名: (2S,3R,4S,5S,6R)-2-(((2R,3S,4R,5R)-5-acetamido-4-acetoxy-2-(acetoxymethyl)-6-hydroxytetrahydro-2H-pyran-3-yl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate；Per-O-acetyl-N-acetyllactosamine；[(2R,3S,4R,5R)-5-acetamido-4-acetyloxy-6-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 68115-84-4
• 化学式: C₂₆H₃₇NO₁₇
• 分子量: 635.576
• InChiKey: PJAVNZGANGVQOC-BKVIZEMQSA-N

物化性质

• 沸点：
  739.3±60.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  44
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  235
• 氢给体数：
  2
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2-deoxy-2-acetamido-3,6-di-O-acetyl-α,β-D-glucopyranose 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以66.667%的产率得到
  参考文献：
  名称：

  One-Step TEMPO-Catalyzed and Water-Mediated Stereoselective Conversion of Glycals into 2-Azido-2-deoxysugars with a PIFA–Trimethylsilyl Azide Reagent System

  摘要：

  An unprecedented water-mediated and TEMPO-catalyzed, one-step, highly regiospecific and stereoselective functionalization of glycals to 2-azido-2-deoxysugars has been developed using a PIFA-Me3SiN3 reagent system in the presence of Bu4NHSO4 as a phase-transfer catalyst. The method is metal-free, proceeds under mild reaction conditions, and tolerates a variety of protecting groups. Using this method, the synthesis of an important trisaccharide unit bound by the monoclonal anti-I Ma antibody has also been demonstrated.

  DOI：

  10.1021/acs.orglett.8b00814
• 作为产物：
  描述：

  1,2',3,3',4',6,6'-hepta-O-acetyl-N-acetyl-β-lactosamine 在 Aspergillusniger lipase immobilized on epoxy sepabeads 作用下， 以 aq. phosphate buffer 、 乙腈 为溶剂， 反应 48.0h， 以50%的产率得到2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2-deoxy-2-acetamido-3,6-di-O-acetyl-α,β-D-glucopyranose
  参考文献：
  名称：

  通过固定化的黑曲霉酯酶催化的水性和非水性介质水解二糖的区域选择性脱乙酰化

  摘要：

  从黑曲霉脂肪酶（ANL）的粗商业提取物中纯化的脂肪酶馏分被选择性地固定在疏水性支持物上。酯酶活性的显着百分比保留在上清液中，该酯酶活性源自无法吸附到所用基质上的酯酶。这些残留的蛋白质被共价固定在环氧丙烯酸树脂上。在水-助溶剂系统中测试了固定化水解酶在乙酰化二糖水解中的作用。ANL-酯酶能够催化C-2位和β- O上的乙酰化β- O-甲基乳糖苷的区域选择性脱保护-甲基乳糖苷位于C-3'位置。从未被报道过的水解产物可以被认为是合成具有生物学意义的寡糖的新基础。此外，还可以在叔丁醇中进行制备性水解。这种溶剂与ANL酯酶的稳定性兼容，并且由于其绿色状态而显得是一种新颖而有前途的方法。

  DOI：

  10.1002/cctc.201300388

文献信息

• One-Step TEMPO-Catalyzed and Water-Mediated Stereoselective Conversion of Glycals into 2-Azido-2-deoxysugars with a PIFA–Trimethylsilyl Azide Reagent System
  作者：Ande Chennaiah、Yashwant D. Vankar

  DOI：10.1021/acs.orglett.8b00814

  日期：2018.5.4

  An unprecedented water-mediated and TEMPO-catalyzed, one-step, highly regiospecific and stereoselective functionalization of glycals to 2-azido-2-deoxysugars has been developed using a PIFA-Me3SiN3 reagent system in the presence of Bu4NHSO4 as a phase-transfer catalyst. The method is metal-free, proceeds under mild reaction conditions, and tolerates a variety of protecting groups. Using this method, the synthesis of an important trisaccharide unit bound by the monoclonal anti-I Ma antibody has also been demonstrated.
• Regioselective Deacetylation of Disaccharides via Immobilized<i>Aspergillus niger</i>Esterase(s)-catalyzed Hydrolysis in Aqueous and Non-aqueous Media
  作者：Teodora Bavaro、Pamela Torres-Salas、Nicola Antonioli、Carlo F. Morelli、Giovanna Speranza、Marco Terreni

  DOI：10.1002/cctc.201300388

  日期：2013.10

  adsorbed onto the employed matrices. These residual proteins were covalently immobilized on epoxy‐acrylic resin. Immobilized hydrolases were tested in the hydrolysis of acetylated disaccharides in water‐cosolvent systems. ANL‐Esterase was able to catalyze regioselective deprotection of acetylated β‐O‐methyl lactoside in C‐2 position and β‐O‐methyl lactosaminide in C‐3′ position. The hydrolyzed products

  从黑曲霉脂肪酶（ANL）的粗商业提取物中纯化的脂肪酶馏分被选择性地固定在疏水性支持物上。酯酶活性的显着百分比保留在上清液中，该酯酶活性源自无法吸附到所用基质上的酯酶。这些残留的蛋白质被共价固定在环氧丙烯酸树脂上。在水-助溶剂系统中测试了固定化水解酶在乙酰化二糖水解中的作用。ANL-酯酶能够催化C-2位和β- O上的乙酰化β- O-甲基乳糖苷的区域选择性脱保护-甲基乳糖苷位于C-3'位置。从未被报道过的水解产物可以被认为是合成具有生物学意义的寡糖的新基础。此外，还可以在叔丁醇中进行制备性水解。这种溶剂与ANL酯酶的稳定性兼容，并且由于其绿色状态而显得是一种新颖而有前途的方法。