Methyl (allyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate | 102965-60-6

• 英文名称: Methyl (allyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate
• 英文别名: methyl (2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-prop-2-enoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• CAS: 102965-60-6
• 化学式: C₁₅H₂₅NO₉
• 分子量: 363.365
• InChiKey: HJQGTZVFZYGLEG-FSTWUICMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Methyl (allyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 四氮唑 、 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 、 溶剂黄146 、 乙腈 为溶剂， 反应 14.83h， 生成 [methyl (5-acetamido-4,7,8-tri-O-acetyl-9-O-dibenzylphosphoryl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosyl)onate] diethyl phosphite
  参考文献：
  名称：

  Base- and Sugar-Modified Cytidine MonophosphateN-Acetylneuraminic Acid (CMP-Neu5Ac) Analogues - Synthesis and Studies with α(2-6)-Sialyltransferase from Rat Liver

  摘要：

  The reaction of sialyl phosphites 1, 22a-d, 28, 39, and 45 with acyl-protected riboside 5-phosphorous acids 2a,b and 23 directly furnished, without addition of a catalyst, under phosphite/phosphate exchange the corresponding beta-configured sialyl riboside monophosphates 3a,b, 24a-d, 29, 46, and 47. The synthesis of the starting materials, formation of the products, and their treatment with sodium methanolate in methanol and subsequent hydrolysis of the sialic acid ester moiety to provide the unprotected target molecules 4a,b, 25a-d, 30, 48, and 49 is described. Investigations with alpha(2-6)-sialyl-transferase from rat Liver showed that base replacement in CMP-Neu5Ac (4a,b) is not tolerated by the enzyme but that modifications of the 5-, 8-, or g-position of the neuraminic acid residue (25a-d, 30, 48, 49) are tolerated.

  DOI：

  10.1002/(sici)1099-0690(200004)2000:8<1467::aid-ejoc1467>3.0.co;2-e
• 作为产物：
  描述：

  N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 在 4 A molecular sieve 、 sodium methylate 、 silver salicylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 Methyl (allyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  Synthesis of protein conjugates and analogues of N-acetylneuraminic acid

  摘要：

  N-乙酰神经酰胺酸（1）是通过改进的程序从中国燕子的唾液腺黏蛋白中制备的，该程序使用酸性树脂水解。化合物1通过新的两步程序转化为已知的乙酰氯乙酰神经酸（3）。对3进行Koenigs-Knorr糖基化，然后通过随后的还原臭氧裂解2-丙烯基α-糖苷制得关键的醛前体7和8，它们通过还原胺化与牛血清白蛋白或破伤风类毒素结合。研究了影响合并程度的因素。还合成了一系列在战略性功能上修改的N-乙酰神经酰胺酸类似物。关键词：唾液酸，N-乙酰神经酰胺酸，新糖蛋白，牛血清白蛋白，破伤风类毒素。

  DOI：

  10.1139/v90-313

文献信息

• Sialic acid dimers
  申请人：Brossmer Reinhard

  公开号：US09260467B2

  公开（公告）日：2016-02-16

  Sialic acid derivatives of the formula (I) in which the symbols have the definitions stated in the description are suitable as medicaments, more particularly for diseases whose course is influenced by Siglec ligands.

  公式（I）中的唾液酸衍生物 其中符号的定义如描述中所述，适用作为药物，更具体地用于受Siglec配体影响的疾病。
• Sialic Acid Derivatives
  申请人：Brossmer Reinhard

  公开号：US20150174262A1

  公开（公告）日：2015-06-25

  A sialic acid derivative of the formula (I), where the symbols are as defined in the description, is suitable for linking with a cargo for regulating metabolic processes, immune reactions, immunizations or desensitizations of the target organism.

  公式（I）的唾液酸衍生物，其中符号如描述中定义的那样，适用于与一种货物连接，用于调节目标生物体的代谢过程、免疫反应、免疫或脱敏。
• Targeting <i>Human</i> CD22/Siglec-2 with Dimeric Sialosides as Novel Oligosaccharide Mimetics
  作者：Horst Prescher、Astrid Schweizer、Martin Frank、Elena Kuhfeldt、Julia Ring、Lars Nitschke

  DOI：10.1021/acs.jmedchem.2c00765

  日期：2022.8.11

  ligands for Siglecs exists due to the various therapeutically relevant functions of these proteins. Here, we report a new strategy to develop and design Siglec ligands as disialyl-oligosaccharide mimetics exemplified on Siglec-2 (CD22). We report insights into development of dimeric ligands with high affinity and avidity to cell surface-expressed CD22, assay development, tool compounds, structure activity

  由于这些蛋白质的各种治疗相关功能，存在对 Siglecs 高亲和力配体开发的重大兴趣。在这里，我们报告了一种开发和设计 Siglec 配体作为二唾液酸寡糖模拟物的新策略，例如 Siglec-2 (CD22)。我们报告了对细胞表面表达的 CD22 具有高亲和力和亲合力的二聚配体的开发、分析开发、工具化合物、结构活性关系以及 B 细胞中钙通量调节的生物学数据的见解。所选配体的结合模式已基于微秒时间尺度上最先进的分子动力学模拟进行建模，提供了配体结合的详细视图，并为 Siglecs 的药物设计工作开辟了新视角。
• Synthesis and inhibitory activity of sialic acid derivatives targeted at viral sialate-O-acetylesterases
  作者：Mathew Stanley、Juliane Mayr、Wolfgang Huber、Reinhard Vlasak、Hansjörg Streicher

  DOI：10.1016/j.ejmech.2011.04.008

  日期：2011.7

  A series of sialosides modified at the 4- and 9-hydroxy group were synthesised and tested for inhibition of the viral haemagglutinin-esterase activity from various Orthomyxoviruses and Coronaviruses. While no inhibition of the sialate-4-O-acetylesterases from mouse hepatitis virus strain S or sialodacryoadenitis virus was found, a 9-O-methyl derivative displayed inhibitory activity against recombinant sialate-9-O-acetylesterase from influenza C virus. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Chemoselective deprotection of acid labile primary hydroxyl protecting groups under CBr4-photoirradiation conditions
  作者：Ming-Yi Chen、Laxmikant N. Patkar、Kuo-Cheng Lu、Adam Shih-Yuan Lee、Chun-Cheng Lin

  DOI：10.1016/j.tet.2004.09.095

  日期：2004.12

  The CBr4-photoirradiation in methanol generates a controlled source of HBr, which can chemoselectively deprotect commonly used hydroxyl-protecting groups in saccharides and nucleosides, such as tert-butyldimethylsilyl, isopropylidene, benzylidene and triphenyl ethers in the presence of other acid-labile functional groups. (C) 2004 Elsevier Ltd. All rights reserved.