Methyl glycosides via Fischer glycosylation: translation from batch microwave to continuous flow processing.

IF 1.7 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY
Monatshefte Fur Chemie Pub Date : 2019-01-01 Epub Date: 2018-11-17 DOI:10.1007/s00706-018-2306-8
Jonas Aronow, Christian Stanetty, Ian R Baxendale, Marko D Mihovilovic
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引用次数: 0

Abstract

Abstract: A continuous flow procedure for the synthesis of methyl glycosides (Fischer glycosylation) of various monosaccharides using a heterogenous catalyst has been developed. In-depth analysis of the isomeric composition was undertaken and high consistency with corresponding results observed under microwave heating was obtained. Even in cases where addition of water was needed to achieve homogeneity-a prerequisite for the flow experiments-no detrimental effect on the conversion was found. The scalability was demonstrated on a model case (mannose) and as part of the target-oriented synthesis of d-glycero-d-manno heptose, both performed on multigram scale.

Graphical abstract:

Abstract Image

Abstract Image

Abstract Image

通过Fischer糖基化的甲基糖苷:从分批微波转化为连续流处理。
摘要:采用非均相催化剂,开发了一种连续流动法合成各种单糖的甲基糖苷(Fischer糖基化)。对异构体的组成进行了深入分析,并获得了与在微波加热下观察到的相应结果的高度一致性。即使在需要添加水以实现均匀性的情况下——流动实验的先决条件——也没有发现对转化率的有害影响。该可扩展性在模型案例(甘露糖)上得到了证明,并作为d-甘油-d-甘露糖庚糖的靶向合成的一部分,这两种合成都是在多图谱规模上进行的。图形摘要:
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来源期刊
Monatshefte Fur Chemie
Monatshefte Fur Chemie 化学-化学综合
CiteScore
3.70
自引率
5.60%
发文量
116
审稿时长
3.3 months
期刊介绍: "Monatshefte für Chemie/Chemical Monthly" was originally conceived as an Austrian journal of chemistry. It has evolved into an international journal covering all branches of chemistry. Featuring the most recent advances in research in analytical chemistry, biochemistry, inorganic, medicinal, organic, physical, structural, and theoretical chemistry, Chemical Monthly publishes refereed original papers and a section entitled "Short Communications". Reviews, symposia in print, and issues devoted to special fields will also be considered.
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