Concise synthesis of zanamivir and its C4-thiocarbamido derivatives utilizing a [3+2]-cycloadduct derived from D-glucono-δ-lactone

被引：19

作者：

Zhu, Xue-Bin ^{[1
]}

Wang, Meng ^{[1
]}

Wang, Shaozhong ^{[1
]}

Yao, Zhu-Jun ^{[1
]}

机构：

[1] Nanjing Univ, State Key Lab Coordinat Chem, Nanjing Natl Lab Microstruct, Inst Chem Biol & Drug Innovat,Sch Chem & Chem Eng, Nanjing 210093, Jiangsu, Peoples R China

来源：

TETRAHEDRON | 2012年 / 68卷 / 08期

关键词：

Zanamivir Sialic acid derivative; D-Glucono-delta-lactone; 1,3-Dipolar cycloaddition; Diastereoselective synthesis; INFLUENZA-VIRUS SIALIDASE; N-ACETYLNEURAMINIC ACID; RECENT PROGRESS; NEURAMINIDASE; INHIBITORS; ANALOGS; SULFUR; C-4;

D O I：

10.1016/j.tet.2012.01.011

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A concise synthesis of zanamivir (GG167, 1) has been accomplished utilizing the adduct of a highly diastereoselective 1,3-dipolar cycloaddition between methyl acrylate and the nitrone derived from D-glucono-delta-lactone. Azide-free introduction of C4 nitrogen functionality and one-pot selective O-acetylation followed by straightforward generation of dihydropyran moiety are two advantages in this synthesis. Using the established methodology and common intermediate, two representative C4-thiocarbamido derivatives of zanamivir were also synthesized. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：2041 / 2044

页数：4

共 22 条

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