Issue 23, 2023

Substrate specific closed-loop optimization of carbohydrate protective group chemistry using Bayesian optimization and transfer learning

Abstract

A new way of performing reaction optimization within carbohydrate chemistry is presented. This is done by performing closed-loop optimization of regioselective benzoylation of unprotected glycosides using Bayesian optimization. Both 6-O-monobenzoylations and 3,6-O-dibenzoylations of three different monosaccharides are optimized. A novel transfer learning approach, where data from previous optimizations of different substrates is used to speed up the optimizations, has also been developed. The optimal conditions found by the Bayesian optimization algorithm provide new insight into substrate specificity, as the conditions found are significantly different. In most cases, the optimal conditions include Et3N and benzoic anhydride, a new reagent combination for these reactions, discovered by the algorithm, demonstrating the power of this concept to widen the chemical space. Further, the developed procedures include ambient conditions and short reaction times.

Graphical abstract: Substrate specific closed-loop optimization of carbohydrate protective group chemistry using Bayesian optimization and transfer learning

Supplementary files

Article information

Article type
Edge Article
Submitted
08 Mar 2023
Accepted
12 May 2023
First published
18 May 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2023,14, 6319-6329

Substrate specific closed-loop optimization of carbohydrate protective group chemistry using Bayesian optimization and transfer learning

N. V. Faurschou, R. H. Taaning and C. M. Pedersen, Chem. Sci., 2023, 14, 6319 DOI: 10.1039/D3SC01261A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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