methyl (3aR,4R,6S,7aS)-3-acetyl-6-(4-methylphenyl)sulfanyl-2-oxo-4-[(1S,2R)-1,2,3-triacetyloxypropyl]-3a,4,7,7a-tetrahydropyrano[3,4-d][1,3]oxazole-6-carboxylate | 1151942-33-4

• 分子结构分类: 有机化合物
• 英文名称: methyl (3aR,4R,6S,7aS)-3-acetyl-6-(4-methylphenyl)sulfanyl-2-oxo-4-[(1S,2R)-1,2,3-triacetyloxypropyl]-3a,4,7,7a-tetrahydropyrano[3,4-d][1,3]oxazole-6-carboxylate
• CAS: 1151942-33-4
• 化学式: C₂₆H₃₁NO₁₂S
• 分子量: 581.598
• InChiKey: YRDIRCKRRXTWGF-RNCZJOPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  186
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl (3aR,4R,6S,7aS)-3-acetyl-6-(4-methylphenyl)sulfanyl-2-oxo-4-[(1S,2R)-1,2,3-triacetyloxypropyl]-3a,4,7,7a-tetrahydropyrano[3,4-d][1,3]oxazole-6-carboxylate 、 双丙酮半乳糖 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.0h， 以95%的产率得到methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosylonate-(2->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside
  参考文献：
  名称：

  α-Selective Sialylations with N-Acetyl-5-N,4-O-Oxazolidinone-Protected p-Toluenethiosialoside

  摘要：

  一种新型的N-乙酰-5-N,4-O-氧杂环丁烷酮保护的对甲苯硫糖苷可以方便地由唾液酸和对甲苯硫醇制备。研究表明，该对甲苯硫糖苷可以成功用于与各种糖苷受体的α-选择性唾液酸化反应，且产率良好。在N-乙酰-5-N,4-O-氧杂环丁烷酮保护的对甲苯硫糖苷与葡萄糖醇的偶联反应中，在-40°C的二氯甲烷-乙腈（2:1）中获得了定量的反应产率和高α-选择性。

  DOI：

  10.1055/s-0028-1087539
• 作为产物：
  描述：

  (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 在 吡啶 、 甲烷磺酸 、 三氟化硼乙醚 、 乙酸酐 、 碳酸氢钠 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 methyl (3aR,4R,6S,7aS)-3-acetyl-6-(4-methylphenyl)sulfanyl-2-oxo-4-[(1S,2R)-1,2,3-triacetyloxypropyl]-3a,4,7,7a-tetrahydropyrano[3,4-d][1,3]oxazole-6-carboxylate
  参考文献：
  名称：

  Comparative studies on the O-sialylation with four different α/β-oriented (N-acetyl)-5-N,4-O-carbonyl-protected p-toluenethiosialosides as donors

  摘要：

  Four types of 5-N,4-O-carbonyl-protected p-toluenethiosialosides were synthesized and their couplings with different acceptors were thoroughly investigated. The results indicate that the sialyl donor structure, the amount of glycosyl acceptor, and the detailed promotion conditions have great influence on the sialylation stereoselectivties and product yields. Under the (p-Tol)(2)SO/Tf2O activation conditions, the glycosylations with simple alcohols provided declined alpha-selectivities and higher yields with increasing the amounts of acceptors from 1.1 equiv to 2.0 equiv. However, the outcome of same sialylation was independent of the relative amounts of sugar alcohol acceptors. With NIS/TfOH as promoter, the alpha-selectivities of the sialylations were significantly improved compared with the cases activated by (p-Tol)(2)SO/Tf2O. In general, the difference in configuration of N-acetylated sialyl donors (D2 and D4) has little effect on the sialylation yield and stereoselectivity. In contrast, the N-deacetylated alpha/beta sialyl donors (D1 and D3) show complex sialylation profiles with different acceptors. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.02.006

文献信息

• Highly efficient α-C-sialylation promoted by (p-Tol)2SO/Tf2O with N-acetyl-5-N,4-O-oxazolidione protected thiosialoside as donor
  作者：Zhen-yuan Gu、Xiao-tai Zhang、Jia-xin Zhang、Guo-wen Xing

  DOI：10.1039/c3ob40876k

  日期：——

  Based on a preactivation protocol with (p-Tol)2SO/Tf2O, a practical, straightforward, and high-yielding synthesis of α-sialyl C-glycosides was accomplished by coupling N-acetyl-5-N,4-O-oxazolidione protected thiosialoside with various trimethylsilyl enol ethers and allyltrimethylsilanes. High yields and excellent α-selectivities were obtained for the strong π-nucleophiles with large nucleophilicity values (N = 4.4–9.0), irrespective of whether silyl enol ethers, silyl ketene acetals or allyltrimethylsilanes were used for the electrophilic C-sialylation.

  基于(p-Tol)2SO/Tf2O预活化策略，通过N-乙酰基-5-N,4-O-恶唑烷酮保护的硫代唾液酸与各种三甲基硅基烯醇醚及烯丙基三甲基硅烷的偶联反应，实现了α-唾液酸型C-糖苷的实用、简便及高产率合成。对于具有大亲核性值（N = 4.4–9.0）的强π-亲核试剂，无论是硅醚烯醇、硅醚乙缩醛还是烯丙基三甲基硅烷作为亲电C-唾液酸化试剂，均能获得高产率和极佳的α-选择性。
• Visible Light Photoredox-Catalyzed <i>O</i>-Sialylation Using Thiosialoside Donors
  作者：Yang Yu、De-Cai Xiong、Run-Ze Mao、Xin-Shan Ye

  DOI：10.1021/acs.joc.6b00999

  日期：2016.8.19

  An efficient protocol for the O-sialylation using thiosialoside donors under visible light photocatalysis was developed. Thiosialosides were activated under the irradiation with blue light in the presence of Ru(bpy)3(PF6)2 as photocatalyst, Umemoto’s reagent as CF3 radical source and Cu(OTf)2 as an additive in acetonitrile/dichloromethane at −30 °C, and the subsequent reaction with glycosyl acceptors

  开发了一种在可见光光催化下使用硫代唾液酸供体的O-唾液酸化的有效方案。在-30°C的乙腈/二氯甲烷中，在Ru（bpy）3（PF 6）2作为光催化剂，Umemoto试剂作为CF 3自由基源和Cu（OTf）2作为添加剂的存在下，在蓝光下激活硫代硫代糖苷。C和随后与糖基受体的反应通常以令人满意的α-选择性以良好至优异的产率产生所需的唾液酸内酯。
• 含唾液酸糖基单元的四苯乙烯化合物、制备方 法和应用
  申请人：北京师范大学

  公开号：CN109929003B

  公开（公告）日：2020-10-02

  本发明涉及利用聚集诱导发光探针检测唾液酸酶活性，具体地，本发明涉及两种含唾液酸糖基单元的四苯乙烯类化合物，其制备方法及在唾液酸酶检测上的应用。本发明中所设计的化合物，具有式(I和II)所示的结构，唾液酸糖基单元为3个或4个，唾液酸糖基是通过三氮唑以及季戊四醇连接到四苯乙烯上。本发明中的化合物可应用于唾液酸酶的检测，在诊断与唾液酸酶相关的疾病中具有应用价值。
• Facile Synthesis of Tumor-Associated Carbohydrate Antigen Ganglioside GM₃from Sialic Acid, Lactose, and Serine
  作者：Guo-wen Xing、Li Chen、Fen-fen Liang

  DOI：10.1002/ejoc.200900778

  日期：2009.12

  Ganglioside GM3 [α-Neu5Ac-(2,3)-β-Gal-(1,4)-β-Glc-(1,1)-Cer; 1] is considered as an important tumor-associated carbohydrate antigen, which can be used in the development of tumor vaccine. In this study, a facile and convergent synthetic strategy for GM3 was developed, and the preparation of three building blocks started from the most readily available compounds sialic acid, lactose, and L-serine. Ceramide

  神经节苷脂 GM3 [α-Neu5Ac-(2,3)-β-Gal-(1,4)-β-Glc-(1,1)-Cer; 1] 被认为是一种重要的肿瘤相关糖类抗原，可用于肿瘤疫苗的开发。在这项研究中，开发了一种简便且收敛的 GM3 合成策略，并从最容易获得的化合物唾液酸、乳糖和 L-丝氨酸开始制备三个构建块。神经酰胺苷元 9 由 L-丝氨酸分 13 步构建，总产率为 6%，而乳糖基三氯乙酰亚胺酯 14 由乳糖分 7 步合成，产率为 25%。以我组开发的新型N-乙酰-5-N,4-O-恶唑烷酮保护的对甲苯硫代唾液酸15为供体，苯甲酰基保护的乳糖神经酰胺二醇23的唾液酸化反应以54%的收率成功完成。我们的策略在五个步骤中提供了更短的 GM3 线性全合成，总产率为 26%。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Electrochemical Assay to Detect Influenza Viruses and Measure Drug Susceptibility
  作者：Xiaohu Zhang、Abasaheb N. Dhawane、Joyce Sweeney、Yun He、Mugdha Vasireddi、Suri S. Iyer

  DOI：10.1002/anie.201412164

  日期：2015.5.11

  An electrochemical assay has been designed to rapidly diagnose influenza viruses. Exposure of a glucose‐bearing substrate to influenza viruses or its enzyme, neuraminidase (NA), releases glucose, which was detected amperometrically. Two methods were used to detect released glucose. First, we used a standard glucose blood meter to detect two viral NAs and three influenza strains. We also demonstrated

  电化学测定被设计用于快速诊断流感病毒。将含葡萄糖的底物暴露于流感病毒或其酶神经氨酸酶（NA），会释放葡萄糖，并通过电流分析法检测到。使用两种方法来检测释放的葡萄糖。首先，我们使用标准血糖仪检测两种病毒 NA 和三种流感病毒株。我们还使用该测定法证明了两种抗病毒药物扎那米韦和奥司他韦的药物敏感性。最后，我们使用一次性试纸在一小时内检测了 19 种 H1N1 和 H3N2 流感病毒株。第一代检测的检测极限和范围分别为 10 2和 10 2 –10 8噬菌斑形成单位 (pfu)。目前的用户友好型血糖仪可以重新用于检测流感病毒。