4-methylphenyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidine1-thio-β-D-galactopyranoside | 942044-14-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methylphenyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidine1-thio-β-D-galactopyranoside
• 英文别名: p-tolyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside；p-tolyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranside
• CAS: 942044-14-6
• 化学式: C₂₉H₃₀O₆S
• 分子量: 506.62
• InChiKey: AKETZSKSEFYVBE-MRMYXZNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.44
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-methylphenyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidine1-thio-β-D-galactopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 硼烷四氢呋喃络合物 、 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 、 三氟甲磺酸二丁硼 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 8.0h， 生成 methyl 2-O-acetyl-3,4-di-O-benzyl-D-glucopyranuronate
  参考文献：
  名称：

  OLIGOSACCHARIDE LINKER, LINKER-PAYLOAD COMPRISING THE SAME AND GLYCAN CHAIN-REMODELED ANTIBODY-DRUG CONJUGATE, PREPARATION METHODS AND USES THEREOF

  摘要：

  The present disclosure further relates to a linker-payload compound including an oligosaccharide group, especially a disaccharide group, where the oligosaccharide group is linked to the remainder of the compound by an amide bond. The present disclosure further relates to an antibody-drug conjugate (ADC) containing the linker-payload compound, where the glycan chain in an antibody is remodeled with the oligosaccharide moiety in the linker-payload compound. The present disclosure further relates to preparation methods and use of the above-mentioned substances.

  公开号：

  US20240082419A1
• 作为产物：
  描述：

  p-methylphenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranoside 在 甲醇 、 camphor-10-sulfonic acid 、 sodium methylate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 40.0h， 生成 4-methylphenyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidine1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  OLIGOSACCHARIDE LINKER, LINKER-PAYLOAD COMPRISING THE SAME AND GLYCAN CHAIN-REMODELED ANTIBODY-DRUG CONJUGATE, PREPARATION METHODS AND USES THEREOF

  摘要：

  The present disclosure further relates to a linker-payload compound including an oligosaccharide group, especially a disaccharide group, where the oligosaccharide group is linked to the remainder of the compound by an amide bond. The present disclosure further relates to an antibody-drug conjugate (ADC) containing the linker-payload compound, where the glycan chain in an antibody is remodeled with the oligosaccharide moiety in the linker-payload compound. The present disclosure further relates to preparation methods and use of the above-mentioned substances.

  公开号：

  US20240082419A1

文献信息

• TMSOTf-Catalyzed Silylation: Streamlined Regioselective One-Pot Protection and Acetylation of Carbohydrates
  作者：A. Abragam Joseph、Ved Prakash Verma、Xin-Yi Liu、Chia-Hui Wu、Vijay M. Dhurandhare、Cheng-Chung Wang

  DOI：10.1002/ejoc.201101267

  日期：2012.2

  A highly efficient TMSOTf-catalyzed HMDS silylation of sugars, which can easily be integrated with subsequent reactions in one-pot fashion, has been developed. Its usefulness was demonstrated by applications to streamlined regioselective one-pot protection and nonenzymatic acetylation of un

  已经开发出一种高效的 TMSOTf 催化的 HMDS 糖基硅烷化，它可以很容易地以一锅法与后续反应相结合。其在简化区域选择性一锅法保护和非酶乙酰化方面的应用证明了其有用性。
• METHOD FOR PREPARING HEXOSE DERIVATIVES
  申请人：Hung Shang Cheng

  公开号：US20090105466A1

  公开（公告）日：2009-04-23

  A method for preparing hexose derivatives comprises the steps of providing a silylated hexose, treating the silylated hexose with a first carbonyl compound in the presence of a catalyst to form an ketalized hexose, treating the ketalized hexose with a second carbonyl compound followed by treating with a first reductant to form an etherized hexose, and converting the etherized hexose into a target hexose derivative, which can be 2-alcohol hexose, 3-alcohol hexose, 4-alcohol hexose, or a 6-alcohol hexose. In particular, the present invention can prepare the hexose derivatives with highly regioselective scheme to protect individual hydroxyls of monosaccharide units and install an orthogonal protecting group pattern in a one-pot manner

  制备己糖衍生物的方法包括以下步骤：提供硅烷基化的己糖，将硅烷基化的己糖与第一羰基化合物在催化剂存在下处理，形成缩酮化的己糖，将缩酮化的己糖与第二羰基化合物处理后，再用第一还原剂处理，形成醚化的己糖，并将醚化的己糖转化为目标己糖衍生物，可以是2-醇己糖、3-醇己糖、4-醇己糖或6-醇己糖。具体来说，本发明可以采用高度选择性的方案制备己糖衍生物，以保护单糖单元的各个羟基，并以一锅法安装正交保护基图案。
• Regioselective one-pot protection, protection–glycosylation and protection–glycosylation–glycosylation of carbohydrates: a case study with<scp>d</scp>-glucose
  作者：Teng-Yi Huang、Medel Manuel L. Zulueta、Shang-Cheng Hung

  DOI：10.1039/c3ob42097c

  日期：——

  carbohydrate synthesis. With the tetra-trimethylsilylated 4-methylphenyl thioglucoside as the starting material, we herein show the one-pot preparations of diols, triols and fully protected derivatives of thioglucosides, and, more importantly, we generated building blocks in situ that effectively acted as glycosyl donors and glycosyl acceptors for further coupling with other monosaccharide building blocks

  定义良好的低聚糖是评估结构与活性之间的关系以破译碳水化合物在各种生理过程中的作用的重要要求。这些寡糖主要通过化学合成获得，尽管近年来取得了许多进步，但是这仍然是一项艰巨的任务。我们先前公开了一种组合的和区域选择性的一锅保护策略，以减少与碳水化合物合成相关的工作量和浪费。以四-三甲基甲硅烷基化的4-甲基苯基硫代葡糖苷为起始原料，我们在此显示了一锅制备的二醇，三醇和硫代葡糖苷的完全保护衍生物，更重要的是，我们就地生成了结构单元有效地充当糖基供体和糖基受体，以进一步与其他单糖结构单元偶联。我们的一锅法保护-糖基化和保护-糖基化-糖基化方法利用了硫糖苷供体之间的可感知反应性差异，可方便地提供二糖和三糖骨架以及最近发现的来自Petrotoga物种的两个嗜热细菌的相容性溶质的骨架。所证明的方案是减少碳水化合物合成中的大量工作并有效递送糖构建体以用于糖生物学的其他领域的又一步。
• Synthesis of ganglioside Hp-s1
  作者：Wan-Shin Chen、Ratnnadeep C. Sawant、Shih-An Yang、Ying-Ju Liao、Jung-Wei Liao、Satpal Singh Badsara、Shun-Yuan Luo

  DOI：10.1039/c4ra08272a

  日期：——

  The complete synthesis of the ganglioside Hp-s1 (1) is described in 10 steps.

  描述了神经节苷脂Hp-s1（1）的完整合成过程，共涉及10个步骤。
• Sub-stoichiometric reductive etherification of carbohydrate substrates and one-pot protecting group manipulation
  作者：Chiao Wen Chen、Ching Chi Wang、Xin Ru Li、Henryk Witek、Kwok-Kong Tony Mong

  DOI：10.1039/d0ob00252f

  日期：——

  its application for one-pot preparation of glycosyl building blocks. The reported procedure features the use of polymethylhydrosiloxane (PMHS) as a sub-stoichiometric reducing agent, which prevents the transilylation side reaction and improves the efficiency of the reductive etherification method. Application of the PMHS reductive etherification procedure for one-pot protecting group manipulation are

  在这项研究中，我们报告了一种新的还原性醚化程序，用于保护碳水化合物底物及其在单罐糖基结构单元制备中的应用。所报道的方法的特征在于使用聚甲基氢硅氧烷（PMHS）作为亚化学计量的还原剂，可防止反硅烷化副反应并提高还原醚化方法的效率。描述了PMHS还原醚化方法在一锅保护基操纵中的应用。