p-tolyl 3,6-di-O-benzyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxy)carbamoylamino-β-D-glucopyranoside | 502692-44-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 3,6-di-O-benzyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxy)carbamoylamino-β-D-glucopyranoside
• 英文别名: 2,2,2-trichloroethyl N-[(2S,3R,4R,5S,6R)-5-hydroxy-2-(4-methylphenyl)sulfanyl-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]carbamate
• CAS: 502692-44-6
• 化学式: C₃₀H₃₂Cl₃NO₆S
• 分子量: 641.012
• InChiKey: MHNOXUPQDRBNCB-FXGKLIOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-tolyl 3,6-di-O-benzyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxy)carbamoylamino-β-D-glucopyranoside 在 吡啶 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.83h， 生成 p-tolyl [3,6-di-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxy)carbonylamino-β-D-glucopyranosyl]-(1→2)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of Sialidase-Resistant Oligosaccharide and Antibody Glycoform Containing α2,6-Linked 3F^ax-Neu5Ac

  摘要：

  Fluorinated glycosides are known to resist the glycosidase-catalyzed glycosidic bond cleavage; however, the synthesis of such glycans, especially 3-fluoro-sialic acid (3F-Neu5Ac) containing sialosides, has been a major challenge. Though the enzymatic synthesis of alpha-2,3-linked 3F-sialosides was reported, until recently there has not been any effective method available for the synthesis of 3F-sialosides in the a-2,6-linkage. In order to understand the biological effect of such modification, we report here a chemical synthesis of 3F(ax)-Neu5Ac-alpha 2,6-Gal as a building block for the assembly of 3Fm-Neu5Ac-containing sialosides and a representative homogeneous antibody glycoform. Our results showed that the sialosides are stable under sialidase catalysis and the rituximab glycoform with a sialylated complex-type biantennary glycan terminated with 3F(ax)-Neu5Ac in the alpha-2,6-linkage (alpha 2,6-F-SCT) has a similar binding avidity as its parent glycoform. These findings open up new opportunities for the development of therapeutic glycoproteins with improved pharmacokinetic parameters.

  DOI：

  10.1021/jacs.9b01991
• 作为产物：
  描述：

  p-methylphenyl 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside 在 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 p-tolyl 3,6-di-O-benzyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxy)carbamoylamino-β-D-glucopyranoside
  参考文献：
  名称：

  碳水化合物底物的亚化学计量还原醚化和一锅保护基操纵。

  摘要：

  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。

  DOI：

  10.1039/d0ob00252f

文献信息

• Screening of Neu5Acα(2–6)gal isomer preferences of siglecs with a sialic acid microarray
  作者：Rohan Yadav、Shani Leviatan Ben-Arye、Balamurugan Subramani、Vered Padler-Karavani、Raghavendra Kikkeri

  DOI：10.1039/c6ob01688j

  日期：——

  The synthesis of Neu5Acα(2–6)Gal structural analogs showed distinct binding patterns with conserved siglecs (hCD22 and mCD22) compared to rapid evolving siglecs (Siglecs -3 & -10).

  Neu5Acα(2–6)Gal结构类似物的合成显示出与保守的siglecs（hCD22和mCD22）相比，与快速进化的siglecs（Siglecs -3和-10）具有不同的结合模式。
• A New Reactivity-Based One-Pot Synthesis of <i>N</i>-Acetyllactosamine Oligomers
  作者：Tony K.-K. Mong、Cheng-Yuan Huang、Chi-Huey Wong

  DOI：10.1021/jo0206420

  日期：2003.3.1

  Poly-N-acetyllactosamine oligomer is a type-2 glycan core from which a number of important bioactive glycoconjugates are assembled in vivo. Development of an effective synthesis of N-acetyllactosamine oligomers will therefore provide a new chemoenzymatic entry to this class of complex saccharides. This paper describes the design and synthesis of thioglycoside building blocks, determination of their

  聚-N-乙酰基乳糖胺低聚物是2型聚糖核，许多重要的生物活性糖结合物都在体内组装而成。因此，开发一种有效合成N-乙酰基乳糖胺低聚物的方法将为这类复杂的糖类提供新的化学酶学入口。本文介绍了硫代糖苷结构单元的设计和合成，它们的相对反应性值的确定，以及它们在各种N-乙酰基乳糖胺低聚物的可编程一锅合成中的应用演示。通过链段缩合的组合，该策略允许以最小的保护基操作来制备较大的寡糖，如在非常短的时间内合成八糖所示。
• Towards Glucosamine Building Blocks: Regioselective One-Pot Protection and Deallylation Procedures
  作者：M. Marques、Ramu Enugala、Luísa Carvalho

  DOI：10.1055/s-0030-1259001

  日期：2010.11

  Glucosamine building blocks have been prepared by an efficient regioselective one-pot protection approach. This synthetic route enabled the straightforward preparation of a glucosamine disaccharide in 73% yield. The system Pd(PPh3)4/TES was investigated as an alternative procedure for anomeric allyl ether deprotection.

  葡萄糖胺结构单元是通过有效的区域选择性一锅保护方法制备的。该合成路线能够直接制备氨基葡萄糖二糖，产率达 73%。研究了 Pd(PPh3)4/TES 系统作为异头烯丙基醚脱保护的替代程序。
• Iterative one-pot syntheses of chitotetroses
  作者：Lijun Huang、Zhen Wang、Xiaoning Li、Xin-shan Ye、Xuefei Huang

  DOI：10.1016/j.carres.2006.01.007

  日期：2006.7

  Rapid syntheses of chitotetrose derivatives were achieved in good yields using the newly developed reactivity independent iterative one-pot strategy. The protective groups on donors and acceptors were independently evaluated allowing matching of the two partners in glycosylation. No anomeric reactivity adjustments or intermediate purification were necessary thus significantly improving the overall synthetic efficiency. Only near stoichiometric amounts of building blocks were required for the assembly of target molecules further highlighting the potential of the iterative one-pot method in complex oligosaccharide synthesis. (c) 2006 Elsevier Ltd. All rights reserved.
• WO2020205034A5
  申请人：——

  公开号：WO2020205034A5

  公开（公告）日：2023-02-16