Methyl (2,3,4-tri-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl)-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside | 302599-14-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl (2,3,4-tri-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl)-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside
• 英文别名: pivaloyl(-6)Gal2Ac3Ac4Ac(b1-3)a-GalNAc1Me；[(2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy-3,4,5-triacetyloxyoxan-2-yl]methyl 2,2-dimethylpropanoate
• CAS: 302599-14-0
• 化学式: C₂₆H₄₁NO₁₅
• 分子量: 607.609
• InChiKey: QEAMEJSRWCSFCC-KNOJGJPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  212
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  Methyl (2,3,4-tri-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl)-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside 在 咪唑 、 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  First total synthesis of sialylated and sulfated Lewisx mucin Core 2 structures as potential tumor associated antigens

  摘要：

  Two branched Core 2 structures, (3-O-SO3Na)Gal beta 1-->4(Fuc alpha 1-->3)GlcNAc beta 1-->6(NeuAc alpha 2-->3Gal beta 1-->3)GalNAc alpha OMe (1) and its positional isomer NeuAc alpha 2-->3Gal beta 1-->4(Fuc alpha 1-->3)GlcNAc beta 1--> 6(3-OSO3Na-Gal beta 1-->3)GalNAc alpha OMe (2), were chemically synthesized for the first time as potential tumor associated antigens. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00975-8
• 作为产物：
  描述：

  Methyl (2,3,4-tri-O-acetyl-6-pivaloyl-β-D-galactopyranosyl)-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside 在 溶剂黄146 作用下， 反应 1.5h， 以70%的产率得到Methyl (2,3,4-tri-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl)-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  从呼吸粘蛋白完全合成唾液酸化和硫酸化的寡糖链。

  摘要：

  据报道，在硫酸化粘蛋白的核心结构中存在的几个复杂的寡糖部分的总合成。通过对甲基（6-O-新戊酰基-β-D-吡喃半乳糖基）（1-> 3）-4,6-O-亚苄基-2-a cetamido-2-deoxy的区域和立体选择性唾液酸化获得三糖受体-α-D-吡喃半乳糖苷与新型唾液酸供体。在成功制备并使用了二糖供体，三糖供体，二糖受体和三糖受体结构单元之后，以可预测和可控制的方式构建了具有高区域和立体选择性的四糖，五糖和六糖。最后，采用温和的氧化裂解方法在存在苄基的情况下选择性去除2-萘甲基（NAP）。

  DOI：

  10.1002/1521-3765(20000915)6:18<3442::aid-chem3442>3.0.co;2-v

文献信息

• Complex Oligosaccharide Investigations:  Synthesis of an Octasaccharide Incorporating the Dimeric Le^x Structure of PSGL-1
  作者：Jie Xia、James L. Alderfer、Robert D. Locke、Conrad F. Piskorz、Khushi L. Matta

  DOI：10.1021/jo020698u

  日期：2003.4.1

  of octasaccharide 3. Toward the preparation of 7, investigations into the influence of different protecting groups upon the relative reactivities of disaccharide acceptor moieties, 25 or 26, and the fucosyl donors, 10 and 11, were conducted using similar glycosylating conditions. Dramatic differences were noted between the effects of electron-donating and electron-withdrawing groups upon the reactivity

  报道了在PSGL-1碳水化合物链中发现的含有二聚Le（x）寡糖结构的八糖的合成。研究了几种使用区域选择性和立体选择性糖基化方法的方法，并制备了一种新型Lewis（x）三糖供体7，并将其用作开发八糖3的开发计划中的关键中间构件。朝着7的制备迈进在相似的糖基化条件下，对不同保护基对二糖受体部分25或26以及岩藻糖基供体10和11的相对反应性的影响进行了研究。在给电子基团和吸电子基团对受体羟基反应性的影响之间发现了显着差异。同样，观察到了对供体分子的糖基化能力的类似作用。供体7的重复使用在合成所需的二聚八糖结构3中发挥了作用。DQF-COSY，TOCSY，ROESY和ESI质谱法充分表征了3和重要中间体的结构和纯度。
• A convergent synthesis of core 2 branched sialylated and sulfated oligosaccharides
  作者：Jie Xia、James L Alderfer、Thamarapu Srikrishnan、E.V Chandrasekaran、Khushi L Matta

  DOI：10.1016/s0968-0896(02)00246-8

  日期：2002.11

  sialylation was accomplished using donor 10 with defined configuration established through X-ray crystallographic analysis. Target oligosaccharides 1-3 were then obtained by the systematic deprotection of intermediates 24, 27 and 29. With these target oligosaccharides 1-3 obtained, biological evaluations of these molecules as enzyme substrates was undertaken and selectin binding studies are planned

  开发了合成核心2寡糖类似物1和2，以及天然形式的唾液酸化和硫酸化六糖3的收敛途径。五糖24、27和六糖28的构建分别通过受体5、7和8中6-OH的完全区域选择性糖基化来实现，这是由于这些中伯羟基的活性远高于仲轴向羟基。结构。使用通过X射线晶体学分析建立的确定构型的供体10完成立体选择性唾液酸化。然后通过中间体24、27和29的系统脱保护获得目标寡糖1-3。用这些目标寡糖1-3，
• The 2-Naphthylmethyl (NAP) Group in Carbohydrate Synthesis: First Total Synthesis of the GlyCAM-1 Oligosaccharide Structures
  作者：Jie Xia、James L. Alderfer、Conrad. F. Piskorz、Khushi L. Matta

  DOI：10.1002/1521-3765(20010119)7:2<356::aid-chem356>3.0.co;2-e

  日期：2001.1.19

  Total syntheses of the GlyCAM-1 (glycosylation-dependent cell adhesion molecule-1) oligosaccharide structures: [alpha-NeuAc-(2 --> 3)-beta-Gal-(1 --> 4)-[alpha-Fuc-(1 --> 3)]-beta-(6-O-SO3Na)-GlcNAc-(1 --> 6)]-[alpha-NeuAc-(2 --> 3)-beta-Gal-(1 --> 3)]-alpha-GalNAc-OMe (1) and [alpha-NeuAc-(2 --> 3)-beta-Gal-(1 --> 4)-[alpha-Fuc-(1 --> 3)]-beta-GlcNAc-(1 --> 6)]-[alpha-NeuAc-(2 3)-beta-Gal-(1 --> 3)]-alpha-GalNAc-OMe (2) through a novel sialyl LewisX tetrasaccharide donor are described. Employing sequential glycosylation strategy, the starting trisaccharide was regio- and stereoselectively constructed through coupling of a disaccharide imidate with the monosaccharide acceptor phenyl-6-O-naphthylmethyl-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside with TMSOTf as a catalyst without affecting the SPh group. The novel sialyl Lewisx tetrasaccharide donor 3 was then obtained by alpha-L-fucosylation of trisaccharide acceptor with the 2,3,4-tri-O-benzyl-1-thio-beta-L-fucoside donor. The structure of the novel sialyl Lewisx tetrasaccharide was established by a combination of 2D DQF-COSY and 2D ROESY experiments. Target oligosaccharides 1 and 2 were eventually constructed through heptasaccharide which was obtained by regioselective assembly of advanced sialyl Lewisx tetrasaccharide donor 3 and a sialylated trisaccharide acceptor in a predictable and controlled manner. Finally, target heptasaccharides 1 and 2 were fully characterized by 2D DQF-COSY, 2D ROESY, HSQC, HMBC experiments and FAB mass spectroscopy.