5-acetamido-2-isopropoxy-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester | 1035355-36-2

• 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: 5-acetamido-2-isopropoxy-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester
• CAS: 1035355-36-2
• 化学式: C₂₁H₃₁NO₁₁
• 分子量: 473.477
• InChiKey: HHMLZZAGNXICNL-FKAKKMJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.17
• 重原子数：
  33.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  152.76
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 45.0h， 生成 5-acetamido-2-isopropoxy-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester 、 5-acetamido-2-isopropoxy-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-2H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Ferrier Glycosylation Reaction Catalyzed by Bi(OTf)3-Montmorillonite K-10: Efficient Synthesis of 3,4-Unsaturated Sialic Acid Derivatives: Synthesis and Biological Evaluation as Inhibitors of Human Parainfluenza Virus Type 1

  摘要：

  The reaction of the 4,5-oxazoline derivative of sialic acid with various alcohols was effectively promoted by a catalytic amount of montmorillonite K-10 clay-supported Bi(OTf)(3) to produce a variety of 3,4-unsaturated sialic acids via the Ferrier glycosylation reaction in moderate yields. The deprotection of the isopropylidene group and hydrolysis of the ester group of 7a-g gave 4a-f, whose inhibitory activities against hPIV-1 sialidase were studied.

  DOI：

  10.3987/com-13-12861

文献信息

• Ferrier Glycosylation Reaction Catalyzed by Bi(OTf)₃-Montmorillonite K-10: Efficient Synthesis of 3,4-Unsaturated Sialic Acid Derivatives
  作者：Kiyoshi Ikeda、Yayoi Ueno、Satoru Kitani、Reiko Nishino、Masayuki Sato

  DOI：10.1055/s-2008-1072649

  日期：——

  The reaction of the 4,5-oxazoline derivative of sialic acid with various alcohols was effectively promoted by a catalytic amount of montmorillonite K-10 clay supported Bi(OTf)3 to produce a variety of 3,4-unsaturated sialic acids via the Ferrier glycosylation reaction in moderate yields.

  在蒙脱石 K-10 粘土支持的 Bi(OTf)3 的催化下，4,5-噁唑啉衍生物硅烷酸与各种醇的反应得到了有效的促进，通过 Ferrier 糖基化反应以中等产率生成了多种 3,4 不饱和硅烷酸。
• 2β-3,4-Unsaturated sialic acid derivatives: Synthesis optimization, and biological evaluation as Newcastle disease virus hemagglutinin-neuraminidase inhibitors
  作者：Paolo La Rocca、Paola Rota、Marco Piccoli、Federica Cirillo、Andrea Ghiroldi、Valentina Franco、Pietro Allevi、Luigi Anastasia

  DOI：10.1016/j.bmc.2020.115563

  日期：2020.7

  The optimization of the synthetic protocol to obtain the 3,4-unsaturated sialic acid derivatives, through the fine-tuning of both the Ferrier glycosylation conditions and the subsequent hydrolysis work-up, is herein reported. The accomplishment of the desired ® -anomers and some selected α-ones, in pure form, led us to evaluate their specific inhibitory activity towards NDV-HN and human sialidase NEU3

  本文报道了通过Ferrier糖基化条件和随后的水解后处理两者的微调来获得3，4-不饱和唾液酸衍生物的合成方案的优化。所需的-端基异构体和一些选定的α-原子的纯净形式，促使我们评估了它们对NDV-HN和人唾液酸酶NEU3的特异性抑制活性。重要的是，所得数据首次允许鉴定三种活性3,4不饱和唾液酸类似物，显示出在微摩尔范围内针对NDV-HN的IC 50值。