ethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-thiogalactopyranoside | 107855-14-1

• 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: ethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-thiogalactopyranoside
• 英文别名: ethyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-β-D-galactopyranoside；[(2R,3S,4S,5R,6S)-4,5-diacetyloxy-6-ethylsulfanyl-2-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 107855-14-1
• 化学式: C₂₁H₂₈O₈S
• 分子量: 440.515
• InChiKey: RKHWYLREGQVNBJ-IFLJBQAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-thiogalactopyranoside 在 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.66h， 生成 Fmoc-Thr(β-6-O-Bn-Gal-(1-3)-α-4,6-O-Bzn-GalNAc)-OtBu
  参考文献：
  名称：

  肿瘤相关的（2,3）-唾液酸-T抗原的仿生合成及其从粘蛋白MUC1和MUC4掺入糖肽抗原中。

  摘要：

  上皮肿瘤细胞上的糖蛋白通常表现出异常的糖基化特征。由葡糖胺转移的下调和唾液酸化过早导致的聚糖侧链的不完全形成导致另外的肽表位，其在粘蛋白型糖蛋白中变得可为免疫系统所接近。这些癌症特异性结构改变被认为是对肿瘤细胞进行选择性免疫攻击的有前途的基础。在与肿瘤相关的糖抗原中，（2,3）-唾液酸-T抗原已被确定为最丰富的聚糖，存在于几种不同的癌细胞系中。根据线性仿生策略，通过保护的半乳糖胺-苏氨酸前体的逐步聚糖链延伸合成（2,3）-唾液酸-T抗原。

  DOI：

  10.1002/chem.200400228
• 作为产物：
  描述：

  6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 ethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-thiogalactopyranoside
  参考文献：
  名称：

  A New Approach to Explore the Binding Space of Polysaccharide-Based Ligands: Selectin Antagonists

  摘要：

  The discovery of molecules that interfere with the binding of a ligand to a receptor remains a topic of great interest in medicinal chemistry. Herein, we report that a monosaccharide unit of a polysaccharide ligand can be replaced advantageously by a conformationally locked acyclic molecular entity. A cyclic component of the selectin ligand Sialyl Lewis(x), GlcNAc, is replaced by an acyclic tether, tartaric esters, which link two saccharide units. The conformational bias of this acyclic tether originates from the minimization of intramolecular dipole-dipole interaction and the gauche effect. The evaluation of the binding of these derivatives to P-selectin was measured by surface plasmon resonance spectroscopy. The results obtained in our pilot study suggest that the discovery of tunable tethers could facilitate the exploration of the carbohydrate recognition domain of various receptors.

  DOI：

  10.1021/ml300263x

文献信息

• Gram scale synthesis of A (type 2) and B (type 2) blood group tetrasaccharides through 1,6-anhydro-N-acetyl-β-D-glucosamine
  作者：Tatiana V. Tyrtysh、Elena Yu. Korchagina、Ivan M. Ryzhov、Nicolai V. Bovin

  DOI：10.1016/j.carres.2017.06.014

  日期：2017.9

  Fuc-Gal-anhydroGlcNAc with single free 3'-OH group. Its standard α-galactosylation gave protected B (type 2) tetrasaccharide. For synthesis of correspondent A tetrasaccharide seven different 2-azido-2-deoxygalactosyl (GalN3) donors were tested: 6-O-acetyl-3,4-O-isopropylidene-GalN3 thioglycoside was shown to provide the best yield (89%) and stereoselectivity (α/β = 24:1). Further 1,6-anhydro cycle opening

  从3-O-苯甲酰基-1，6-脱水-N-乙酰基葡糖胺开始，提出了以3-氨基丙基糖苷形式的A（2型）和B（2型）四糖的革兰氏合成。其半乳糖基化，然后再保护，得到具有单个游离2'-OH基团的乳糖胺衍生物，总产率为75％。标准岩藻糖基化和下一轮再保护的总产率为88％，得到具有单个游离3'-OH基团的三糖Fuc-Gal-anhydroGlcNAc。其标准的α-半乳糖基化得到保护的B（2型）四糖。为了合成对应的A四糖，测试了七个不同的2-叠氮基-2-脱氧半乳糖基（GalN3）供体：6-O-乙酰基-3,4-O-异亚丙基-GalN3硫代糖苷提供了最佳收率（89％），立体选择性（α/β= 24：1）。进一步打开1,6-脱水循环，
• Convergent synthesis of the tetrasaccharide repeating unit of the cell wall lipopolysaccharide of <i>Escherichia coli</i> O40
  作者：Abhijit Sau、Anup Kumar Misra

  DOI：10.3762/bjoc.8.230

  日期：——

  A tetrasaccharide repeating unit corresponding to the cell-wall lipopolysaccharide of E. coli O40 was synthesized by using a convergent block glycosylation strategy. A disaccharide donor was coupled to a disaccharide acceptor by a stereoselective glycosylation. A 2-aminoethyl linker was chosen as the anomeric protecting group at the reducing end of the tetrasaccharide. All glycosylation steps are significantly

  通过使用收敛阻断糖基化策略合成了对应于大肠杆菌 O40 细胞壁脂多糖的四糖重复单元。二糖供体通过立体选择性糖基化与二糖受体偶联。选择 2-氨基乙基接头作为四糖还原端的异头保护基团。所有糖基化步骤的产量和立体选择性都非常高。
• Chemical and chemoenzymatic syntheses of sialyl Lewisa tetrasaccharide antigen
  作者：Yuanyuan Jiang、Shichao Duan、Jiaming Li、Yanli Zhao、Jinsong Yang

  DOI：10.1039/d4ob00809j

  日期：——

  Sialyl Lewisa (sLea), also known as cancer antigen 19-9, is a tumor-associated carbohydrate antigen. In this article, chemical and chemoenzymatic syntheses of a tetrasaccharide glycan 1 structurally derived from sLea are reported. Challenges involved in the chemical synthesis include the highly stereoselective construction of 1,2-cis-α-L-fucoside and α-D-sialoside, as well as the assembly of the 3

  Sialyl Lewis a (sLe a )，也称为癌抗原 19-9，是一种肿瘤相关碳水化合物抗原。在这篇文章中，报道了结构上源自 sLe a的四糖聚糖1的化学和化学酶合成。化学合成中涉及的挑战包括1,2-顺式-α- L-岩藻糖苷和α -D-唾液酸苷的高度立体选择性构建，以及3,4-二取代的N-乙酰葡糖胺亚基的组装。全苄化硫代岩藻糖苷和N-乙酰基-5- N ,4- O-恶唑烷酮保护的唾液酸硫代糖苷分别作为糖基供体，有效制备了所需的α-岩藻糖苷和α-唾液酸苷。 3,4-支链葡糖胺主链通过3- O然后4- O糖基化序列建立，其中葡糖胺部分的3-羟基首先被糖基化，然后是4-羟基。还利用了一种简便的化学酶方法来合成目标分子。化学获得的游离二糖30以酶催化的区域和立体特异性方式依次唾液酸化和岩藻糖基化，以高产率形成1 。附加的接头1可以共价连接至载体蛋白以用于进一步的免疫学研究。
• The synthesis of linear trilactosamine
  作者：G. V. Pazynina、V. V. Severov、N. V. Bovin

  DOI：10.1134/s1068162008050129

  日期：2008.9

  TrilactosamineGal beta 1-4GlcNAc beta 1-3Gal beta 1-4GlcNAc beta 1-3Gal beta 1-4GlcNAc beta-sp, where sp = O(CH(2))(3)NH(2) is a spacer, was synthesized. The tetrasaccharide fragment Gal beta 1-4GlcNAc beta 1-3Gal beta 1-4GlcNAc beta-sp was obtained by successive glycosylation using elongation by one monosaccharide residue at a time; and the tetrasaccharide was then transformed into a hexasaccharide with a disaccharide glycosyl donor. A 2,2,2-trichloroethoxycarbonyl group was used for the protection of the glucosamine amino group.
• EFFICIENT SYNTHESIS OF POLYLACTOSAMINE STRUCTURES THROUGH REGIOSELECTIVE GLYCOSYLATIONS1
  作者：Therese Buskas、Peter Konradsson、Stefan Oscarson

  DOI：10.1081/car-100108275

  日期：——

  Di-, tri- and tetramers of beta-(1 -->3)-linked N-acetyllactosamine residues have been synthesised as their methyl glycosides, to be used in ITC binding studies to various galectins. The synthetic strategy involves two types of regioselective glycosylations: couplings of a galactosyl donor to 3,4-diol N-tetrachlorophthalimido glucose acceptors to give the lactosamine monomer building blocks, and subsequent formation of the oligomers through consecutive couplings of lactosamine donors to 2',3',4'-lactosamine acceptors, with high selectivity for the desired products.