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Sialylation reactions with 5-N,7-O-carbonyl-protected sialyl donors: unusual stereoselectivity with nitrile solvent assistance.使用5-N,7-O-羰基保护的唾液酸供体的唾液酸化反应：腈溶剂辅助下的异常立体选择性。
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本文引用的文献

1
Further studies on cation clock reactions in glycosylation: observation of a configuration specific intramolecular sulfenyl transfer and isolation and characterization of a tricyclic acetal.糖基化中阳离子时钟反应的进一步研究：构型特异性分子内亚磺酰基转移的观察以及三环缩醛的分离与表征
Carbohydr Res. 2016 Jun 2;427:21-8. doi: 10.1016/j.carres.2016.03.028. Epub 2016 Apr 6.
2
Exploration of the Oxazolidinthione Protecting System for the Synthesis of Sialic Acid Glycosides.用于唾液酸糖苷合成的恶唑烷硫酮保护体系的探索
J Carbohydr Chem. 2013;32(5-6):324-335. doi: 10.1080/07328303.2013.804081. Epub 2013 Sep 2.
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Oxidative Deamination of N-Acetyl Neuraminic Acid: Substituent Effects and Mechanism.N-乙酰神经氨酸的氧化脱氨作用：取代基效应与机制
J Am Chem Soc. 2016 Jan 27;138(3):1084-92. doi: 10.1021/jacs.5b13015. Epub 2016 Jan 15.
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Cation Clock Reactions for the Determination of Relative Reaction Kinetics in Glycosylation Reactions: Applications to Gluco- and Mannopyranosyl Sulfoxide and Trichloroacetimidate Type Donors.用于测定糖基化反应中相对反应动力学的阳离子时钟反应：在葡萄糖基和甘露糖基亚砜以及三氯乙酰亚胺酯型供体中的应用
J Am Chem Soc. 2015 Aug 19;137(32):10336-45. doi: 10.1021/jacs.5b06126. Epub 2015 Aug 7.
5
The isothiocyanato moiety: an ideal protecting group for the stereoselective synthesis of sialic acid glycosides and subsequent diversification.异硫氰酸酯部分：用于唾液酸糖苷立体选择性合成及后续多样化修饰的理想保护基。
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The intriguing dual-directing effect of 2-cyanobenzyl ether for a highly stereospecific glycosylation reaction.2-氰基苄基醚对高度立体选择性糖苷化反应的奇特双重导向效应。
Nat Commun. 2014 Oct 3;5:5051. doi: 10.1038/ncomms6051.
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A propos of glycosyl cations and the mechanism of chemical glycosylation; the current state of the art.关于糖基阳离子与化学糖基化机制；当前的技术水平
Carbohydr Res. 2015 Feb 11;403:48-59. doi: 10.1016/j.carres.2014.06.020. Epub 2014 Jul 1.
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Dissecting the influence of oxazolidinones and cyclic carbonates in sialic acid chemistry.剖析噁唑烷酮和环状碳酸酯在唾液酸化学中的影响。
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Cation clock permits distinction between the mechanisms of α- and β-O- and β-C-glycosylation in the mannopyranose series: evidence for the existence of a mannopyranosyl oxocarbenium ion.阳离子钟可区分α-O-和β-O-以及β-C-甘露糖苷在甘露糖系列中的作用机制：存在甘露吡喃糖氧鎓离子的证据。
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Highly alpha-selective sialyl phosphate donors for efficient preparation of natural sialosides.用于高效制备天然唾液酸苷的高α-选择性唾液酸磷酸供体。
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邻苯二甲醇唾液酸单酯的合成及分子内糖基化反应。供体构型和氮保护基对环化产率和选择性的重要性；一种表明乙腈参与反应的N-唾液酰乙酰胺的分离与表征

Synthesis and intramolecular glycosylation of sialyl mono-esters of o-xylylene glycol. The importance of donor configuration and nitrogen protecting groups on cyclization yield and selectivity; isolation and characterization of a N-sialyl acetamide indicative of participation by acetonitrile.

作者信息

Amarasekara Harsha, Crich David

机构信息

Department of Chemistry, Wayne State University, Detroit, MI 48202, USA.

Department of Chemistry, Wayne State University, Detroit, MI 48202, USA.

出版信息

Carbohydr Res. 2016 Nov 29;435:113-120. doi: 10.1016/j.carres.2016.09.019. Epub 2016 Oct 8.

DOI:10.1016/j.carres.2016.09.019
PMID:27744142
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5110385/
Abstract

The synthesis and cyclization reactions, leading to spirocyclic medium ring-sized diolides, of o-(hydroxymethyl)xylylene monoesters of sialyl thioglycosides is described. Cyclization yields and stereoselectivities are found to vary as a function of the anomeric stereochemistry of the thioglycoside and of the N5 protecting group, and these effects are discussed in terms of the reaction mechanism. Cyclization in the presence of acetonitrile results in the isolation and characterization of a Ritter-type N-sialyl acetamide, which affords strong evidence for the participation of acetonitrile in the form of sialyl nitrilium ions.

摘要

描述了唾液酸硫代糖苷的邻（羟甲基）亚二甲苯基单酯合成并环化生成螺环中环大小的二内酯的反应。发现环化产率和立体选择性随硫代糖苷的异头立体化学和N5保护基的变化而变化，并根据反应机理讨论了这些影响。在乙腈存在下进行环化反应，得到并表征了一种里特型N-唾液酰乙酰胺，这为乙腈以唾液酰腈离子的形式参与反应提供了有力证据。