Automated, Multistep Continuous-Flow Synthesis of 2,6-Dideoxy and 3-Amino-2,3,6-trideoxy Monosaccharide Building Blocks,Angewandte Chemie International Edition

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Automated, Multistep Continuous-Flow Synthesis of 2,6-Dideoxy and 3-Amino-2,3,6-trideoxy Monosaccharide Building Blocks
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2021-08-30 , DOI: 10.1002/anie.202109887
Subbarao Yalamanchili ₁ , Tu-Anh Nguyen ₁ , Alexander Zsikla ₁ , Gavin Stamper ₂ , Ashley E DeYong ₂ , John Florek ₁ , Olivea Vasquez ₁ , Nicola L B Pohl ₂ , Clay S Bennett ₁

Affiliation

An automated continuous flow system capable of producing protected deoxy-sugar donors from commercial material is described. Four 2,6-dideoxy and two 3-amino-2,3,6-trideoxy sugars with orthogonal protecting groups were synthesized in 11–32 % overall yields in 74–131.5 minutes of total reaction time. Several of the reactions were able to be concatenated into a continuous process, avoiding the need for chromatographic purification of intermediates. The modular nature of the experimental setup allowed for reaction streams to be split into different lines for the parallel synthesis of multiple donors. Further, the continuous flow processes were fully automated and described through the design of an open-source Python-controlled automation platform.

中文翻译：

2,6-二脱氧和 3-氨基-2,3,6-三脱氧单糖结构单元的自动化、多步连续流合成

描述了一种能够从商业材料中产生受保护的脱氧糖供体的自动连续流动系统。在 74-131.5 分钟的总反应时间内合成了四种带有正交保护基的 2,6-二脱氧糖和两种 3-氨基-2,3,6-三脱氧糖，总产率为 11-32%。几个反应能够串联成一个连续的过程，避免了中间体的色谱纯化的需要。实验装置的模块化性质允许将反应流分成不同的线路，以并行合成多个供体。此外，连续流程是完全自动化的，并通过开源 Python 控制的自动化平台的设计进行了描述。

更新日期：2021-10-12

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