D-Glucose- and D-mannose-based antimetabolites. Part 2. Facile synthesis of 2-deoxy-2-halo-D-glucoses and -D-mannoses

Fokt I; Szymanski S; Skora S; Cybulski M; Madden T; Priebe W

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D-Glucose- and D-mannose-based antimetabolites. Part 2. Facile synthesis of 2-deoxy-2-halo-D-glucoses and -D-mannoses

机译：基于D-葡萄糖和D-甘露糖的抗代谢物。第2部分。2-脱氧-2-卤代-D-葡萄糖和-D-甘露糖的简便合成

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Modified D-glucose and D-mannose analogs are potentially clinically useful metabolic inhibitors. Biological evaluation of 2-deoxy-2-halo analogs has been impaired by limited availability and lack of efficient methods for their preparation. We have developed practical synthetic approaches to 2-deoxy-2-fluoro-, 2-chloro-2-deoxy-, 2-bromo-2-deoxy-, and 2-deoxy-2-iodo derivatives Of D-glucose and D-mannose that exploit electrophilic addition reactions to a commercially available 3,4,6-tri-O-acetyl-D-glucal.

机译：修饰的D-葡萄糖和D-甘露糖类似物可能是临床上有用的代谢抑制剂。 2-脱氧-2-卤代类似物的生物学评估由于有限的可用性和缺乏有效的制备方法而受到损害。我们已经开发出实用的合成方法来合成D-葡萄糖和D-葡萄糖的2-脱氧-2-氟-，2-氯-2-脱氧-，2-溴-2-脱氧和2-脱氧-2-碘的衍生物甘露糖利用亲电加成反应到市售的3,4,6-三-O-乙酰基-D-葡萄糖。

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《Carbohydrate research》 |2009年第12期|共10页
作者
Fokt I; Szymanski S; Skora S; Cybulski M; Madden T; Priebe W;
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正文语种 eng
中图分类有机化学;
关键词
2-Deoxy-2-halo-D-glucose; 2-Deoxy-2-halo-D-mannose; Inhibitors of glycolysis; Synthesis;

机译：2-脱氧-2-卤代-D-葡萄糖;2-脱氧-2-卤代-D-甘露糖;糖酵解抑制剂;合成;

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1. D-Glucose- and D-mannose-based antimetabolites. Part 2. Facile synthesis of 2-deoxy-2-halo-D-glucoses and -D-mannoses [J] . Fokt I, Szymanski S, Skora S, Carbohydrate research . 2009,第12期

机译：基于D-葡萄糖和D-甘露糖的抗代谢物。第2部分。2-脱氧-2-卤代-D-葡萄糖和-D-甘露糖的简便合成
2. D-Glucose and d-mannose-based metabolic probes. Part 3: Synthesis of specifically deuterated d-glucose, d-mannose, and 2-deoxy-d-glucose [J] . Fokt I., Skora S., Conrad C., Carbohydrate research . 2013,第Null期

机译：基于D-葡萄糖和D-甘露糖的代谢探针。第3部分：特定氘代d-葡萄糖，d-甘露糖和2-deoxy-d-葡萄糖的合成
3. Asymmetric phase transfer Darzens reactions catalyzed by d-glucose- and d-mannose-based chiral crown ethers [J] . Rapi Z., Bakó P., Keglevich G., Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2012,第6a7期

机译：d-葡萄糖和d-甘露糖基手性冠醚催化不对称相转移Darzens反应
4. Facile one-pot synthesis of freestanding carbon nanotubes on cellulose-derived carbon films for supercapacitor applications: effect of the synthesis temperature [C] . Witawat Singsang, Manop Panapoy, Bussarin Ksapabutr Eco-Energy and Materials Science and Engineering . 2014

机译：适用于超级电容器应用纤维素衍生碳膜上独立碳纳米管的单壶合成：合成温度的效果
5. Part I. Asymmetric synthesis of bicyclic analogues of risedronate as molecular probes of the mechanism of action of bisphosphonate antiosteoporotic drugs and potentially more efficacious antiosteoporotic agents. Part II. Facile preparation and functionalization of chiral stabilized ylides from common chiral auxiliaries using the Bestmann ylide and their use in Wittig reactions. Part III. Asymmetric organocatalysis: 1. An investigation of alpha-hydroxylation of aldehydes; 2. Synthesis of a novel camphor-based alpha-aminotetrazole organocatalyst. [D] . Song, Xinyi. 2007

机译：第一部分：利塞膦酸盐双环类似物的不对称合成，作为双膦酸盐类抗骨质疏松药和潜在更有效的抗骨质疏松药作用机理的分子探针。第二部分使用Bestmann内酯从常见手性助剂轻松制备和官能化手性稳定化的叶基及其在Wittig反应中的用途。第三部分不对称有机催化：1.醛的α-羟基化研究； 2.合成新的基于樟脑的α-氨基四唑有机催化剂。
6. d-Glucose and d-mannose-based metabolic probes. Part 3: Synthesis of specifically deuterated d-glucose d-mannose and 2-deoxy-d-glucose [O] . Izabela Fokt, Stanislaw Skora, Charles Conrad, -1

机译：D-葡萄糖和基于D-甘露糖的代谢探针。第3部分：特别是氘代D-葡萄糖D-甘露糖和2-脱氧-D-葡萄糖的合成
7. d-Glucose and d-mannose-based metabolic probes. Part 3: Synthesis of specifically deuterated d-glucose, d-mannose, and 2-deoxy-d-glucose [O] . Izabela Fokt, Stanislaw Skora, Charles Conrad, 2013

机译：D-葡萄糖和基于D-甘露糖的代谢探针。第3部分：特别是氘代D-葡萄糖，D-甘露糖和2-脱氧-D-葡萄糖的合成

D-Glucose- and D-mannose-based antimetabolites. Part 2. Facile synthesis of 2-deoxy-2-halo-D-glucoses and -D-mannoses

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