methyl (p-tolyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-α,β-D-galacto-non-2-ulopyranoside)onate | 1219717-80-2

• 分子结构分类: 有机化合物
• 英文名称: methyl (p-tolyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-α,β-D-galacto-non-2-ulopyranoside)onate
• CAS: 1219717-80-2
• 化学式: C₂₆H₃₁NO₁₂S
• 分子量: 581.598
• InChiKey: YRDIRCKRRXTWGF-GPIKNWLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.91
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  161.04
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  methyl (p-tolyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-α,β-D-galacto-non-2-ulopyranoside)onate 、 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99%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：

  Studies on the sialylation of galactoses with different C-5 modified sialyl donors

  摘要：

  Synthetic sialylated glycans provide useful tools to study carbohydrate-mediated biological recognition; however chemical sialylation is the most challenging practice in preparative carbohydrate chemistry, which is often associated with low yields and poor stereoselectivity. Herein, we conducted extensive studies on sialylation with five types of 5-N-modified sialyl donors and four types of galactosyl acceptors. Our studies have shown that a good combination between the donor and the acceptor seems necessary to achieve high yield and stereoselectivity. None of the donors or acceptors showed 'universal' utility toward the sialylation reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.08.007
• 作为产物：
  描述：

  methyl (4S,5R,6R)-5-amino-4-hydroxy-2-(4-methylphenyl)sulfanyl-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate 在 吡啶 、 碳酸氢钠 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 methyl (p-tolyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-α,β-D-galacto-non-2-ulopyranoside)onate
  参考文献：
  名称：

  Studies on the sialylation of galactoses with different C-5 modified sialyl donors

  摘要：

  Synthetic sialylated glycans provide useful tools to study carbohydrate-mediated biological recognition; however chemical sialylation is the most challenging practice in preparative carbohydrate chemistry, which is often associated with low yields and poor stereoselectivity. Herein, we conducted extensive studies on sialylation with five types of 5-N-modified sialyl donors and four types of galactosyl acceptors. Our studies have shown that a good combination between the donor and the acceptor seems necessary to achieve high yield and stereoselectivity. None of the donors or acceptors showed 'universal' utility toward the sialylation reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.08.007

文献信息

• Total synthesis of the aminopropyl functionalized ganglioside GM1
  作者：Bin Sun、Bo Yang、XueFei Huang

  DOI：10.1007/s11426-011-4449-x

  日期：2012.1

  GM1 is a common ganglioside pentasaccharide present on mammalian cell surface. It has been shown to play important roles in cellular communications and initiation of β-amyloid aggregation. In order to synthesize GM1, an efficient synthetic route was developed via a [3+2] strategy. The GM3 trisaccharide acceptor bearing an azido propyl group at the reducing end was prepared using the traditional acetamide

  GM 1是存在于哺乳动物细胞表面的常见神经节苷脂五糖。已经表明它在细胞通讯和β-淀粉样蛋白聚集的起始中起重要作用。为了合成GM 1，通过[3 + 2]策略开发了有效的合成途径。使用传统的乙酰胺保护的唾液酸基硫糖基供体制备了在还原端带有叠氮丙基的GM 3三糖受体，该化合物的立体选择性比三氯乙酰胺或恶唑烷酮保护的唾液酸供体更好。GM 3轴向4-羟基的糖基化发现二糖供体的β-糖基化高度依赖于供体保护基。带有更刚性的亚苄基的供体给出低的糖基化产率。用乙酸酯取代亚苄基导致有效的偶联和完全保护的GM 1五糖的形成。通过氨基丙基侧链官能化的五糖产生的GM 1的脱保护，这将是生物学研究的宝贵探针。
• Highly Alpha-Selective Sialyl Phosphate Donors for Efficient Preparation of Natural Sialosides
  作者：Che-Hsiung Hsu、Kuo-Ching Chu、Yih-Shyan Lin、Jeng-Liang Han、Yu-Shiang Peng、Chien-Tai Ren、Chung-Yi Wu、Chi-Huey Wong

  DOI：10.1002/chem.200903035

  日期：2010.2.8

  Hubble, bubble, toil, and trouble: The use of a new sialyl phosphate donor allows the stereoselective, one‐pot multicomponent synthesis of α‐sialooligosaccharides (see scheme).

  哈勃，气泡，辛劳和麻烦：使用新的唾液酸磷酸酯供体可以立体选择性地单锅多组分合成α-唾液寡糖（参见方案）。
• Synthesis and Bioassay of Neurogenically Potent Gangliosides DSG-A, Hp-s1 and Their Analogues
  作者：Ganesh B. Shelke、Yu-Hsuan Lih、Ying-Ju Liao、Chih-Wu Liang、Tzer-Min Kuo、Ying-Chin Ko、Shun-Yuan Luo

  DOI：10.1021/acschemneuro.8b00055

  日期：2018.6.20

  the search of a potent candidate for neurotherapy, we designed and synthesized various analogues of ganglioside Hp-s1. The modification includes the change in hydrophobicity by varying the carbon chain length, altering the number of hydrogen bonds, and replacing the anomeric atom. The chemical synthesis was carried out by using various methods and discussed in details. The neuritogenic activities of

  为了寻找有效的神经疗法候选人，我们设计并合成了神经节苷脂Hp-s1的各种类似物。所述修饰包括通过改变碳链长度，改变氢键的数目并替换异头原子来改变疏水性。化学合成通过使用各种方法进行并详细讨论。在人神经母细胞瘤细胞系SH-SY5Y中证实了这些类似物的神经生成活性。发现神经节苷脂Hp-s1类似物比神经节苷脂Hp-s1具有更高的IL-17A转录上调活性。
• Chemical and chemoenzymatic syntheses of sialyl Lewisa tetrasaccharide antigen
  作者：Yuanyuan Jiang、Shichao Duan、Jiaming Li、Yanli Zhao、Jinsong Yang

  DOI：10.1039/d4ob00809j

  日期：——

  Sialyl Lewisa (sLea), also known as cancer antigen 19-9, is a tumor-associated carbohydrate antigen. In this article, chemical and chemoenzymatic syntheses of a tetrasaccharide glycan 1 structurally derived from sLea are reported. Challenges involved in the chemical synthesis include the highly stereoselective construction of 1,2-cis-α-L-fucoside and α-D-sialoside, as well as the assembly of the 3

  Sialyl Lewis a (sLe a )，也称为癌抗原 19-9，是一种肿瘤相关碳水化合物抗原。在这篇文章中，报道了结构上源自 sLe a的四糖聚糖1的化学和化学酶合成。化学合成中涉及的挑战包括1,2-顺式-α- L-岩藻糖苷和α -D-唾液酸苷的高度立体选择性构建，以及3,4-二取代的N-乙酰葡糖胺亚基的组装。全苄化硫代岩藻糖苷和N-乙酰基-5- N ,4- O-恶唑烷酮保护的唾液酸硫代糖苷分别作为糖基供体，有效制备了所需的α-岩藻糖苷和α-唾液酸苷。 3,4-支链葡糖胺主链通过3- O然后4- O糖基化序列建立，其中葡糖胺部分的3-羟基首先被糖基化，然后是4-羟基。还利用了一种简便的化学酶方法来合成目标分子。化学获得的游离二糖30以酶催化的区域和立体特异性方式依次唾液酸化和岩藻糖基化，以高产率形成1 。附加的接头1可以共价连接至载体蛋白以用于进一步的免疫学研究。