[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate]-(2->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetoimidate | 99270-74-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate]-(2->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetoimidate
• 英文别名: [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate]-(2->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate；[methyl (4''',5''',7''',8''',9'''-penta-O-acetyl-α-neuramin)ate]yl-(2'''->3'')-2'',4'',6''-tri-O-acetyl-β-galactopyranosyl-(1''->4')-2',3',6'-tri-O-acetyl-α-glucopyranosyl trichloroacetimidate
• CAS: 99270-74-3
• 化学式: C₄₆H₆₁Cl₃N₂O₂₉
• 分子量: 1212.35
• InChiKey: OGSBHDLSOJBPPU-XMNGUEANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.06
• 重原子数：
  80.0
• 可旋转键数：
  22.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  397.63
• 氢给体数：
  2.0
• 氢受体数：
  30.0

反应信息

• 作为反应物：
  描述：

  [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate]-(2->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetoimidate 在 偶氮二异丁腈 、 MS 4 Angstroem 、 三氟化硼乙醚 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2R,3S,4S,5R,6S)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-(5-acetylsulfanylpentoxy)oxan-3-yl]oxyoxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  An alternative route for the construction of carbosilane dendrimers uniformly functionalized with lactose or sialyllactose moieties

  摘要：

  A new approach for the formation of an acetylthio linkage on aglycon by means of a radical addition of thioacetic acid into the C-C double bond of the aglycon was examined. An introduction of a carbohydrate moiety into carbosilane dendrimers was demonstrated using a one-pot coupling reaction in MeOH-DMF in the presence of NaOMe via removal of an acetyl group of the acetylthio linkage in the saccharide moieties, producing a thiolate anion and a nucleophilic replacement of the thiolate to dendric alkyl bromide to form carbosilane dendrimers uniformly bearing lactose or sialyllactose moieties through thioether linkages in high yields. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00422-1
• 作为产物：
  描述：

  三氯乙腈 、 [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate]-(2->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-D-glucopyranose 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate]-(2->3)-2,4,6-tri-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl trichloroacetimidate 、 [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate]-(2->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetoimidate
  参考文献：
  名称：

  合成唾液酸-3'-乳糖的 3-氨基丙基 β-糖苷和衍生的新糖缀合物作为肿瘤疫苗原型和用于控制免疫反应的人工抗原

  摘要：

  从代表肿瘤相关神经节苷脂 GM3 碳水化合物部分的生物技术上可用的三糖唾液酸-3'-乳糖开始，合成了相应的 3-氨基丙基 β-糖苷 (1) 和 3-(4-maleimidobutanoylamino) 丙基糖苷。后者与 Megathura crenulata 血蓝蛋白 (KLH) 的硫醇化衍生物反应得到碳水化合物-蛋白质偶联物，这是一种肿瘤疫苗原型，含有约 330 个与 KLH 相连的三糖配体。配体 1 的 N-硬脂酰化提供了模型新糖脂，用于比较研究单价和多价免疫原和天然神经节苷脂 GM3 的活性。还制备了单价缀合物，其中配体 1 通过低聚（乙二醇）间隔物与生物素连接，以及多价缀合物与聚丙烯酰胺载体。

  DOI：

  10.1007/s11172-006-0554-y

文献信息

• The total synthesis of ganglioside GM3
  作者：Richard I. Duclos

  DOI：10.1016/s0008-6215(00)00121-x

  日期：2000.10

  beta-Gal-(1'' --> 3'/4')-GlcNAc alpha-(2''' --> 3'')-sialyltransferase enzyme, and was evaluated as a synthetic intermediate to ganglioside GM3. The chemical total synthesis of ganglioside GM3 was performed on one of the largest scales yet reported. The highlights of this synthesis include minimizing the steps necessary to prepare the lactosyl acceptor as a useful anomeric mixture, which was present in

  审查了神经节苷脂GM3（NeuAc alpha3Gal beta4Glc beta1Cer）的先前合成，并研究了化学酶和化学全合成方法。在化学酶学方法中，（2S，3R，4E）-5'''-乙酰基-α-神经氨酸-（2'''-> 3''）-β-吡喃半乳糖基-（1''-> 4'使用重组β-Gal-（1''-> 3'可以轻松制备）-β-吡喃葡萄糖基-（1'-> 1）-2-叠氮基-4-十八碳烯1，，3-二醇（azidoGM3） / 4'）-GlcNAcα-（2'''-> 3''）-唾液酸转移酶，被评估为神经节苷脂GM3的合成中间体。神经节苷脂GM3的化学全合成以迄今报道的最大规模之一进行。该合成的亮点包括最小化制备作为有用的异头混合物的乳糖基受体所必需的步骤，对于与已知神经氨酰基供体的高度区域选择性和相当立体选择性的唾液酸化，过量存在以得到被保护的GM3三糖。合成方法通过充分表征的GM3三糖三氯乙亚氨
• Preparation of glycopolymers having sialyl α2 → 3 lactose moieties as the potent inhibitors for mumps virus
  作者：Koji Matsuoka、Takayuki Kaneshima、Ryota Adachi、Jiei Sasaki、Takao Hashiguchi、Tetsuo Koyama、Takahiko Matsushita、Ken Hatano

  DOI：10.1016/j.bmcl.2021.128389

  日期：2021.11

  A water-soluble glycomonomer having a sialyl α2 → 3 lactose (SLac) moiety was prepared from a known imidate derivative of the SLac and an acrylamide alcohol by means of Schmidt’s protocol followed by transesterification. Polymerization of the monomer proceeded in water as the solvent in the presence of ammonium persulfate (APS)—tetramethylethylenediamine (TEMED). Since acryl amide (AAm) was used as

  具有唾液酸 α2 → 3 乳糖 (SLac) 部分的水溶性糖单体由已知的 SLac 亚胺酸酯衍生物和丙烯酰胺醇通过施密特方案随后酯交换制备。在过硫酸铵（APS）-四甲基乙二胺（TEMED）的存在下，单体的聚合在作为溶剂的水中进行。由于丙烯酰胺（AAm）被用作糖密度排列的调节剂，因此获得了三种糖密度不同的糖聚合物。使用糖聚合物对 Vero 细胞进行腮腺炎病毒 (MuV) 感染抑制试验，结果表明糖密度低的糖聚合物具有最高的抑制效力。与唾液酸化 Lewis X (SLe X) 作为先前研究中最强的抑制剂，具有低糖密度的 SLac 聚合物显示出比 SLe x强十倍的抑制效力。这一发现表明，具有适当空间排列的单体 SLac 的多价转化能够有效抑制 MuV 的附着糖蛋白与 Vero 细胞上聚糖受体之间的相互作用。
• Syntheses and biological evaluations of carbosilane dendrimers uniformly functionalized with sialyl α(2→3) lactose moieties as inhibitors for human influenza viruses
  作者：Hiroyuki Oka、Tomotsune Onaga、Tetsuo Koyama、Chao-Tan Guo、Yasuo Suzuki、Yasuaki Esumi、Ken Hatano、Daiyo Terunuma、Koji Matsuoka

  DOI：10.1016/j.bmc.2009.06.035

  日期：2009.8

  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.
• Synthetic assembly of a series of glycopolymers having sialyl α2-3 lactose moieties connected with longer spacer arms
  作者：Ryota Adachi、Takahiko Matsushita、Tetsuo Koyama、Ken Hatano、Koji Matsuoka

  DOI：10.1016/j.bmc.2023.117209

  日期：2023.3