Simple Synthesis of Conformationally Fixed Glycosamine Analogues by Beckmann Rearrangement at the Carbohydrate Ring

Umbreen Sumaira; Linker Torsten

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Simple Synthesis of Conformationally Fixed Glycosamine Analogues by Beckmann Rearrangement at the Carbohydrate Ring

机译：通过在碳水化合物环的贝克曼重排简单合成构象固定的糖胺类似物

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Conformationally fixed carbohydrate analogues are promising small-molecule inhibitors for hydrolases like O-GlcNAcase (OGA); however, their synthesis usually requires many steps. Herein we describe cycloadditions of dichloroketene to various glycals and subsequent Beckmann rearrangements, which offer an easy and stereoselective entry to glycosamine derivatives in good yields. The reactions are applicable for hexoses, pentoses, and disaccharides, and transformations to the corresponding imidates proceed smoothly. First biological tests reveal that such imidates indeed inhibit human OGA.

机译：构象固定的碳水化合物类似物是有前景的水解酶小分子抑制剂，例如O-GlcNAcase（OGA）;但是，它们的合成通常需要许多步骤。在本文中，我们描述了二氯乙烯烯与各种糖的环加成以及随后的贝克曼重排，这提供了容易且立体选择性地以良好的产率进入糖胺衍生物。该反应适用于己糖，戊糖和二糖，并且转化为相应的酰亚胺的过程进展顺利。最初的生物学测试表明，这些酰亚胺确实抑制了人类的OGA。

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《Chemistry: A European journal》 |2015年第20期|共5页
作者
Umbreen Sumaira; Linker Torsten;
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正文语种 eng
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carbohydrates; cycloaddition; enzyme inhibitors; rearrangement; selective syntheses;

机译：碳水化合物;环加成;酶抑制剂;重排;选择性合成;

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1. Simple Synthesis of Conformationally Fixed Glycosamine Analogues by Beckmann Rearrangement at the Carbohydrate Ring [J] . Umbreen Sumaira, Linker Torsten Chemistry: A European journal . 2015,第20期

机译：通过在碳水化合物环的贝克曼重排简单合成构象固定的糖胺类似物
2. Synthesis of a tricyclic lactam via Beckmann rearrangement and ring-rearrangement metathesis as key steps [J] . Sambasivarao Kotha, Ongolu Ravikumar, Jadab Majhi Beilstein journal of organic chemistry. . 2015,第1期

机译：通过贝克曼重排和环重排复分解法合成三环内酰胺是关键步骤
3. Synthesis of a tricyclic lactam via Beckmann rearrangement and ring-rearrangement metathesis as key steps [J] . Sambasivarao Kotha, Ongolu Ravikumar, Jadab Majhi Beilstein journal of organic chemistry. . 2015,第1期

机译：通过贝克曼重排和环重排复分解法合成三环内酰胺是关键步骤
4. Design and synthesis of an amide-linked angiotensin II analogue with 3,5 side chain bridge:structural resemblance of ring cluster conformation with AT_1 non-peptide antagonists [C] . Panagiota Roumelioti, Ludmila Polevaya, Nektarios Giatas, the International Peptide Symposium . 2001

机译：与3,5侧链桥的酰胺连接血管紧张素II类似物的设计与合成：与AT_1非肽拮抗剂的环形簇构象的结构相似
5. I. Total synthesis and application of fluorophore-labeled didemnin and tamandarin analogues. II. Synthetic approaches to pondaplin and analogues. III. Yohimbanones: Formation and reaction via novel rearrangements. [D] . Leonard, Michael Scot. 2003

机译：I.荧光团标记的双嘧达明和坦丹林类似物的全合成和应用。二。假单胞菌素及其类似物的合成方法。三，育亨宾酮：通过新颖的重排形成和反应。
6. Synthesis of a tricyclic lactam via Beckmann rearrangement and ring-rearrangement metathesis as key steps [O] . Sambasivarao Kotha, Ongolu Ravikumar, Jadab Majhi 2015

机译：通过贝克曼重排和环重排复分解合成三环内酰胺是关键步骤
7. Synthesis of a tricyclic lactam via Beckmann rearrangement and ring-rearrangement metathesis as key steps [O] . KOTHA, S, RAVIKUMAR, O, MAJHI, J 2015

机译：通过贝克曼重排和环重排复分解合成三环内酰胺是关键步骤

Simple Synthesis of Conformationally Fixed Glycosamine Analogues by Beckmann Rearrangement at the Carbohydrate Ring

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