methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,3-dibromo-2,3,5-trideoxy-β-D-erythro-L-manno-non-2-ulopyranosonate | 108999-04-8

• 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-2,3-dibromo-2,3,5-trideoxy-β-D-erythro-L-manno-non-2-ulopyranosonate
• 英文别名: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,3-dibromo-2,3,5-trideoxy-β-D-erythro-L-manno-2-nonulopyranosonate；methyl (2S,3R,4R,5S,6R)-5-acetamido-4-acetyloxy-2,3-dibromo-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 108999-04-8
• 化学式: C₂₀H₂₇Br₂NO₁₂
• 分子量: 633.242
• InChiKey: DSCLWCGSKWCYFK-CIVJTVJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.28
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  169.83
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,3-dibromo-2,3,5-trideoxy-β-D-erythro-L-manno-non-2-ulopyranosonate 在 水 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以82%的产率得到methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate
  参考文献：
  名称：

  Access to 3-O-Functionalized N-Acetylneuraminic Acid Scaffolds

  摘要：

  Direct access to 3-O-functionalized 2-alpha-Nacetylneurarninides and their corresponding 2,3-dehydro-2-deoxy-N-acetylneuraminic acid derivatives is described. Initially, a stereoselective ring-opening of the key intermediate N-acetylneuraminic acid (Neu5Ac) 2,343-epoxide with an alcohol provided the 3-hydroxy alpha-glycoside. O-Allcylation of the C3 hydroxyl group generated novel 3-O-functionalized Neu5Ac derivatives that provided the corresponding unsaturated derivatives upon elimination.

  DOI：

  10.1021/acs.joc.5b00992
• 作为产物：
  描述：

  methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 在 sodium bromide 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以98%的产率得到methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,3-dibromo-2,3,5-trideoxy-β-D-erythro-L-manno-non-2-ulopyranosonate
  参考文献：
  名称：

  Functionalization of 2-Deoxy-2,3-dehydro-N-acetylneuraminic Acid Methyl Ester

  摘要：

  乙酰基保护的2-脱氧-2,3-脱氢神经氨酸甲酯通过修饰其2,3-双键进行功能化，将其转化为新的糖基供体，例如2,3-二溴-、2,3-环氧-和2-卤代-3-羟基神经氨酸衍生物。

  DOI：

  10.1246/bcsj.60.631

文献信息

• [EN] ANTI -INFLUENZA AGENTS<br/>[FR] AGENTS ANTIGRIPPAUX
  申请人：UNIV GRIFFITH

  公开号：WO2011006208A1

  公开（公告）日：2011-01-20

  The present invention relates to compounds that selectively inhibit influenza A virus group (1) sialidases and are therefore potential anti-influenza agents.

  本发明涉及选择性抑制流感A病毒群（1）唾液酸酶的化合物，因此是潜在的抗流感药物。
• ANTI-INFLUENZA AGENTS
  申请人：Von Itzstein Mark

  公开号：US20120202877A1

  公开（公告）日：2012-08-09

  The present invention relates to compounds that selectively inhibit influenza A virus group (1) sialidases and are therefore potential anti-influenza agents.

  本发明涉及选择性抑制流感A病毒群（1）唾液酸酶的化合物，因此是潜在的抗流感药物。
• A Stereospecific Synthesis of β-Glycosides of<i>N</i>-Acetylneuraminic Acid and Secondary Alcohols
  作者：Kaoru Okamoto、Tadao Kondo、Toshio Goto

  DOI：10.1246/cl.1986.1449

  日期：1986.9.5

  Glycosylation of secondary alcohols such as cholesterol, methyl 2,4,6-tri-O-benzylgalactopyranoside, and 2-deoxy-2,3-dehydro-NeuAc methyl ester with a new glycosyl donor, 2β,3α-dibromo-2-deoxy-NeuAc methyl ester, selectively gave the corresponding β-glycosides in high yields. The 3α-bromo-glycosides were debrominated with tri-n-butylstannane to the corresponding glycosides, which were deprotected to

  仲醇如胆固醇、甲基 2,4,6-tri-O-benzylgalactopyranoside 和 2-deoxy-2,3-dehydro-NeuAc 甲酯与新的糖基供体 2β,3α-dibromo-2-deoxy 的糖基化-NeuAc 甲酯，选择性地以高产率得到相应的 β-糖苷。3α-溴-糖苷用三正丁基锡烷脱溴为相应的糖苷，将其脱保护得到具有β-NeuAc的游离糖苷。
• Synthesis and Biological Evaluation of Several Dephosphonated Analogues of CMP-Neu5Ac as Inhibitors of GM3-Synthase
  作者：Paola Rota、Federica Cirillo、Marco Piccoli、Antonio Gregorio、Guido Tettamanti、Pietro Allevi、Luigi Anastasia

  DOI：10.1002/chem.201501770

  日期：2015.10.5

  hypoxic stress, suggesting that a pharmacological inhibition of the GM3 synthesis could be instrumental for the development of new treatments for ischemic diseases. Herein, the synthesis of several dephosphonated CMP‐Neu5Ac congeners and their anti‐GM3‐synthase activity is reported. Biological activity testes revealed that some inhibitors almost completely blocked the GM3‐synthase activity in vitro and reduced

  先前的研究表明，降低成肌细胞中GM3的含量会增强细胞对缺氧应激的抵抗力，这表明对GM3合成的药理抑制作用可能有助于开发缺血性疾病的新疗法。在这里，有几个dephosphonated CMP-Neu5Ac的同类物的合成及其抗-报道GM3合酶活性。生物活性睾丸显示，一些抑制剂在体外几乎完全阻断了GM3合酶的活性，并降低了活的胚胎肾脏293A细胞中GM3的含量，最终激活了表皮生长因子受体（EGFR）信号级联。
• Sim, Mui Mui; Kondo, Hirosato; Wong, Chi-Huey, Journal of the American Chemical Society, 1993, vol. 115, # 6, p. 2260 - 2267
  作者：Sim, Mui Mui、Kondo, Hirosato、Wong, Chi-Huey

  DOI：——

  日期：——