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钯催化2-碘糖的羰基化反应,以甲酸作为羰基源合成C-2羧酸和醛。

Palladium catalysed carbonylation of 2-iodoglycals for the synthesis of C-2 carboxylic acids and aldehydes taking formic acid as a carbonyl source.

作者信息

Ahmed Ajaz, Hussain Nazar, Bhardwaj Monika, Chhalodia Anuj Kumar, Kumar Amit, Mukherjee Debaraj

机构信息

Academy of Scientific and Innovative Research India.

Natural Product Chemistry Division, Indian Institute of Integrative Medicine India

出版信息

RSC Adv. 2019 Jul 17;9(39):22227-22231. doi: 10.1039/c9ra03626a.

Abstract

Pd catalyzed carbonylative reaction of 2-iodo-glycals has been developed taking formic acid as a carbonyl source for the synthesis of 2-carboxylic acids of sugars by the hydroxycarbonylation strategy. The methodology was successfully extended to the synthesis of 2-formyl glycals by using a reductive carbonylation approach. Both ester and ether protected glycals undergo the reaction and furnished sugar acids in good yield which is otherwise not possible by literature methods. The C-2 sugar acids were successfully utilized for the construction of 2-amido glycals, 2-dipeptido-glycal by Ugi reaction and C-1 and C-2 branched glycosyl esters.

摘要

已经开发出钯催化的2-碘代糖烯的羰基化反应,以甲酸作为羰基源,通过羟基羰基化策略合成糖类的2-羧酸。该方法成功扩展到通过还原羰基化方法合成2-甲酰基糖烯。酯和醚保护的糖烯均能发生反应,并以良好的产率得到糖酸,而这是文献方法无法实现的。C-2糖酸已成功用于通过Ugi反应构建2-氨基糖烯、2-二肽基糖烯以及C-1和C-2支链糖基酯。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5230/9066652/e0a964192570/c9ra03626a-s2.jpg

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