methyl (lauryl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate | 821796-99-0

• 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: methyl (lauryl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate
• 英文别名: methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-dodecylsulfanyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 821796-99-0
• 化学式: C₃₂H₅₃NO₁₂S
• 分子量: 675.838
• InChiKey: XGRWMLJNFIYXET-HDJPIGHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  46
• 可旋转键数：
  26
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  195
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl (lauryl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 (2R,4S,5R,6R)-4-Acetoxy-5-azido-2-cyclohexyloxy-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of a useful lauryl thioglycoside of sialic acid and its application

  摘要：

  An efficient synthesis of a useful thioglycosyl donor 2 was accomplished directly from known peracetylated sialic acid methvl ester and 1-dodecanethiol (lauryl mercaptan) in the presence of BF3-OEt2. The reactivities of the lauryl glycosides for glycosidation by means of TMSOTf as a convenient promoter were investigated, and the lauryl thioglycoside showed satisfactory activities. Further transformation of the lauryl glycoside was also attempted to give a 5-azide analogue 14 of the sialic acid, which was also reacted with a secondary alcohol in the presence of TMSOTf to give known glycoside 15 in high yield. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.105
• 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 、 十二硫醇 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以26.2%的产率得到methyl (lauryl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  Syntheses and biological evaluations of carbosilane dendrimers uniformly functionalized with sialyl α(2→3) lactose moieties as inhibitors for human influenza viruses

  摘要：

  A series of carbosilane dendrimers uniformly functionalized with sialyl lactose moieties (Neu5Ac alpha 2 -> 3-Gal beta 1 -> 4Glc) was systematically synthesized, and biological evaluations for anti-influenza virus activity using the glycodendrimers were performed. The results suggested that the glycodendrimers had unique biological activities depending on the form of their core frame, and Dumbbell(1)6-amide type glycoden-drimer 7 showed particularly strong inhibitory activities against human influenza viruses [A/PR/8/34 (H1N1) and A/Aichi/2/68 (H3N2)]. The results suggested that the structure-activity relationship (SAR) on the glycolibrary against various influenza viruses was observed, and dumbbell-shaped dendrimers as supporting carbohydrate moieties were found to be the most suitable core scaffolds in this study. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.035

文献信息

• Synthesis of sialic acid derivatives having a CC double bond substituted at the C-5 position and their glycopolymers
  作者：Kaori Suzuki、Jun-Ichi Sakamoto、Tetsuo Koyama、Sangchai Yingsakmongkon、Yasuo Suzuki、Ken Hatano、Daiyo Terunuma、Koji Matsuoka

  DOI：10.1016/j.bmcl.2009.07.034

  日期：2009.9

  Glycomonomers of sialic acid in which the acetamide group at C-5 was converted into two kinds of CC double bond substituents were prepared and the fully protected glycomonomers were directly polymerized before deprotection steps. Radical polymerization with acrylamide in DMF in the presence of ammonium persulfate and N,N,N’,N’-tetramethylethylenediamine proceeded smoothly and gave corresponding sialopolymers

  制备了唾液酸的共聚单体，其中在C-5处的乙酰胺基被转化为两种CC双键取代基，并且在脱保护步骤之前将完全保护的糖单体直接聚合。在过硫酸铵和N，N，N'，N'-四甲基乙二胺的存在下，在DMF中用丙烯酰胺进行的自由基聚合反应顺利进行，得到相应的唾液聚合物。有趣的是，糖单体不仅对人流感病毒株的H1N1具有血凝抑制活性，而且对H3N2也具有血凝抑制活性。
• Synthesis and biological evaluation of sialic acid derivatives containing a long hydrophobic chain at the anomeric position and their C-5 linked polymers as potent influenza virus inhibitors
  作者：Kaori Suzuki、Tetsuo Koyama、Sangchai Yingsakmongkon、Yasuo Suzuki、Ken Hatano、Koji Matsuoka

  DOI：10.1016/j.bmc.2011.10.064

  日期：2012.1

  deprotection to furnish water-soluble glycopolymers. The activities of the deprotected glycopolymers and glycomonomers against human influenza viruses (H1N1 and H3N2) and avian influenza virus (H5N3) were evaluated. Biological evaluations showed that the glycomonomers containing a long hydrophobic chain at the anomeric position had both hemagglutination and neuraminidase inhibitory activities.

  在Shotten-Baumann条件下，将唾液酸中的C-5乙酰胺基转化为两种C C双键取代基。可聚合的糖单体在异头位置也含有疏水链或羟基。在过硫酸铵（APS）和N，N，N '，N的存在下，用丙烯酰胺进行完全保护的糖单体的自由基聚合。'-四甲基乙二胺（TEMED），然后脱保护得到水溶性糖聚合物。评估了脱保护的糖聚合物和糖单体对人流感病毒（H1N1和H3N2）和禽流感病毒（H5N3）的活性。生物学评估表明，在异头位置含有长疏水链的糖单体具有血凝作用和神经氨酸酶抑制活性。
• Use of an oxazolidinone derivative of a sialyl thioglycoside as a useful glycosyl donor for α-favorable glycosidation with simple alcohols
  作者：Jianhong Zhang、Tetsuo Koyama、Takahiko Matsushita、Ken Hatano、Koji Matsuoka

  DOI：10.1016/j.tetlet.2024.155189

  日期：2024.8

  thioglycoside with simple alcohols proceeded smoothly to yield the corresponding α-glycosides in good yields after isolation. The results suggested that the glycosylation reaction using the oxazolidinone derivative of sialic acid has excellent α-stereoselectivity and enables easy isolation of the desired product from the reaction mixture.

  从已知的 Neu5Ac 硫代糖苷中高效合成了衍生自 β-乙酰基神经氨酸的恶唑烷酮月桂基硫代糖苷。通过三氟甲磺酸三甲基甲硅烷基酯（TMSOTf）和碘代琥珀酰亚胺（NIS）作为组合介体系统评估了恶唑烷酮的β-糖苷化反应活性。月桂基硫代糖苷与简单醇的糖苷化反应顺利进行，分离后以良好的产率生成相应的α-糖苷。结果表明，使用唾液酸恶唑烷酮衍生物的糖基化反应具有优异的α-立体选择性，并且能够容易地从反应混合物中分离出所需产物。