methyl (4S,5R,6R)-4-acetyloxy-5-(1,3-dioxoisoindol-2-yl)-2-[N-phenyl-C-(trifluoromethyl)carbonimidoyl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate | 874904-93-5

• 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 (4S,5R,6R)-4-acetyloxy-5-(1,3-dioxoisoindol-2-yl)-2-[N-phenyl-C-(trifluoromethyl)carbonimidoyl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 874904-93-5
• 化学式: C₃₄H₃₃F₃N₂O₁₄
• 分子量: 750.636
• InChiKey: GIOLOHNHMXVCBK-VZELBCTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  53
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  200
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  methyl (4S,5R,6R)-4-acetyloxy-5-(1,3-dioxoisoindol-2-yl)-2-[N-phenyl-C-(trifluoromethyl)carbonimidoyl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate 、 allyl 2-O-benzoyl-6-O-benzyl-α-D-galactopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 various solvent(s) 为溶剂， 反应 0.08h， 以77%的产率得到
  参考文献：
  名称：

  Highly Efficient α‐Sialylation by Virtue of Fixed Dipole Effects ofN‐Phthalyl Group: Application to Continuous Flow Synthesis of α(2‐3)‐and α(2‐6)‐Neu5Ac‐Gal Motifs by Microreactor

  摘要：

  Highly alpha-selective sialylation of sialic acid N-phenyltrifluoroacetimidate with various galactose and lactose acceptors has been achieved by introducing the C-5 N-phthalyl group on the donor. The "fixed dipole effect" of the N-phthalyl group was proposed to explain the high reactivity and a-selectivity. The microfluidic system was applied to the present alpha-sialylation, which is amenable to large-scale synthesis. The N-phthalyl group was removed by treatment with methylhydrazine acetate, for which protocol can be readily applied to the synthesis of a variety of sialic acid-containing oligosaccharides.[GRAPHICS]

  DOI：

  10.1080/07328300701634796
• 作为产物：
  描述：

  、 2,2,2-三氟-N-苯基亚氨代乙酰氯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 生成 methyl (4S,5R,6R)-4-acetyloxy-5-(1,3-dioxoisoindol-2-yl)-2-[N-phenyl-C-(trifluoromethyl)carbonimidoyl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  Highly Efficient α‐Sialylation by Virtue of Fixed Dipole Effects ofN‐Phthalyl Group: Application to Continuous Flow Synthesis of α(2‐3)‐and α(2‐6)‐Neu5Ac‐Gal Motifs by Microreactor

  摘要：

  Highly alpha-selective sialylation of sialic acid N-phenyltrifluoroacetimidate with various galactose and lactose acceptors has been achieved by introducing the C-5 N-phthalyl group on the donor. The "fixed dipole effect" of the N-phthalyl group was proposed to explain the high reactivity and a-selectivity. The microfluidic system was applied to the present alpha-sialylation, which is amenable to large-scale synthesis. The N-phthalyl group was removed by treatment with methylhydrazine acetate, for which protocol can be readily applied to the synthesis of a variety of sialic acid-containing oligosaccharides.[GRAPHICS]

  DOI：

  10.1080/07328300701634796

文献信息

• Renaissance of Traditional Organic Reactions under Microfluidic Conditions: A New Paradigm for Natural Products Synthesis
  作者：Katsunori Tanaka、Koichi Fukase

  DOI：10.1021/op900084f

  日期：2009.9.18

  synthesis for bioactive natural products is described. Efficient procedures using the microfluidic system were developed for the large-scale synthesis of important synthetic units of asparagine-linked oligosaccharide in glycoprotein. Advantageous aspects of microfluidic conditions, i.e., efficient mixing, fast heat transfer, and residence time control led to cation-mediated reactions, such as α-sialylation

  描述了生物活性天然产物的连续流合成。开发了使用微流体系统的有效程序，用于大规模合成糖蛋白中天冬酰胺连接的寡糖的重要合成单元。微流体条件的有利方面，即有效的混合，快速的传热和停留时间的控制导致阳离子介导的反应，例如α-唾液酸化，β-甘露糖基化和亚苄基乙缩醛基团的还原打开，产率高。开发了微流体脱水用于工业规模合成免疫刺激性天然萜类化合物烷。在水性双相系统中碱介导的羟醛缩合使得能够以高产率合成β-羟基酮。
• One-Pot Synthesis of<i>N</i>-Acetyl- and<i>N</i>-Glycolylneuraminic Acid Capped Trisaccharides and Evaluation of Their Influenza A(H1 N1) Inhibition
  作者：Yun Hsu、Hsiu-Hwa Ma、Larry S. Lico、Jia-Tsrong Jan、Koichi Fukase、Yosuke Uchinashi、Medel Manuel L. Zulueta、Shang-Cheng Hung

  DOI：10.1002/anie.201309646

  日期：2014.2.24

  N‐acetylneuraminic acid (Neu5Ac) α(2→6)‐linked to galactose (Gal) as binding sites for influenza virus hemagglutinin. N‐Glycolylneuraminic acid (Neu5Gc) in place of Neu5Ac is known to affect hemagglutinin binding in other species. Not normally generated by humans, Neu5Gc may find its way to human cells from dietary sources. To compare their influence in influenza virus infection, six trisaccharides with Neu5Ac

  人肺上皮细胞天然地提供与半乳糖（Gal）连接的末端N-乙酰神经氨酸（Neu5Ac）α（2→6）-作为流感病毒血凝素的结合位点。已知用N-乙二醇神经氨酸（Neu5Gc）替代Neu5Ac会影响其他物种中的血凝素结合。Neu5Gc通常不是人类产生的，它可能会通过饮食来源找到进入人体细胞的途径。为了比较它们对流感病毒感染的影响，使用一锅装配和发散转化制备了六种带有与Gal相连的Neu5Ac或Neu5Gcα（2→6）和不同还原糖单位的三糖。糖组件使用N邻苯二甲酰基保护的亚氨基唾液酸亚胺酸酯，可与硫代半乳糖苷进行化学选择性活化和α-立体选择性偶联。对细胞病变作用的评估表明，Neu5Gc封端的三糖对病毒感染的抑制作用优于其Neu5Ac对应物。
• Concise and Reliable Syntheses of Glycodendrimers via Self-Activating Click Chemistry: A Robust Strategy for Mimicking Multivalent Glycan–Pathogen Interactions
  作者：Kindi Farabi、Yoshiyuki Manabe、Hiroaki Ichikawa、Shuto Miyake、Masato Tsutsui、Kazuya Kabayama、Toshiyuki Yamaji、Katsunori Tanaka、Shang-Cheng Hung、Koichi Fukase

  DOI：10.1021/acs.joc.0c01547

  日期：2020.12.18

  Individual interactions between glycans and their receptors are usually weak, although these weak interactions can combine to realize a strong interaction (multivalency). Such multivalency plays a crucial role in the recognition of host cells by pathogens. Glycodendrimers are useful materials for the reconstruction of this multivalent interaction. However, the introduction of a large number of glycans to a dendrimer core is fraught with difficulties. We herein synthesized antipathogenic glycodendrimers using the self-activating click chemistry (SACC) method developed by our group. The excellent reactivity of SACC enabled the efficient preparation of sialyl glycan and Gb3 glycan dendrimers, which exhibited strong avidity toward hemagglutinin on influenza virus and Shiga toxin B subunit produced by Escherichia coli, respectively. We demonstrated the usefulness of SACC-based glycodendrimers as antipathogenic compounds.