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三氟甲磺酸铟催化碳水化合物的全乙酰化反应。

Indium triflate catalyzed peracetylation of carbohydrates.

作者信息

Bizier Nicholas P, Atkins Shannon R, Helland Luke C, Colvin Shane F, Twitchell Joseph R, Cloninger Mary J

机构信息

Department of Chemistry and Biochemistry, Montana State University, Bozeman, MT 59717, USA.

出版信息

Carbohydr Res. 2008 Jul 21;343(10-11):1814-8. doi: 10.1016/j.carres.2008.04.009. Epub 2008 Apr 10.

Abstract

Peracetylation is a very common protection strategy that is widely implemented in carbohydrate synthesis. Here, a method for the peracetylation of carbohydrates using catalytic In(OTf)(3) in neat acetic anhydride is reported. In(OTf)(3) has low toxicity and is mild and water tolerant, and the reactions are high yielding and efficient. Details regarding the scope and mechanism of the reaction are briefly discussed.

摘要

全乙酰化是一种非常常见的保护策略,在碳水化合物合成中广泛应用。本文报道了一种在纯乙酸酐中使用催化量的三氟甲磺酸铟(In(OTf)(3))对碳水化合物进行全乙酰化的方法。三氟甲磺酸铟毒性低,性质温和且耐水,反应产率高且高效。文中简要讨论了该反应的适用范围和机理细节。

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本文引用的文献

1
Magnesium bistrifluoromethanesulfonimide as a new and efficient acylation catalyst.
J Org Chem. 2006 Jul 21;71(15):5785-8. doi: 10.1021/jo0605142.
2
InCl3 as a powerful catalyst for the acetylation of carbohydrate alcohols under microwave irradiation.
Carbohydr Res. 2005 May 23;340(7):1387-92. doi: 10.1016/j.carres.2005.03.001.
3
HClO4-SiO2 catalyzed per-O-acetylation of carbohydrates.
Carbohydr Res. 2005 Feb 7;340(2):325-9. doi: 10.1016/j.carres.2004.11.021.
6
7
Catalytic nucleophilic acyl substitution of anhydrides by amphoteric vanadyl triflate.
Org Lett. 2001 Nov 15;3(23):3729-32. doi: 10.1021/ol016684c.
9
Highly Efficient and Versatile Acylation of Alcohols with Bi(OTf)(3) as Catalyst.
Angew Chem Int Ed Engl. 2000 Aug 18;39(16):2877-2879. doi: 10.1002/1521-3773(20000818)39:16<2877::aid-anie2877>3.0.co;2-v.

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