Bayesian Optimization-Assisted Screening to Identify Improved Reaction Conditions for Spiro-Dithiolane Synthesis

Bayesian optimization (BO)-assisted screening was applied to identify improved reaction conditions toward a hundred-gram scale-up synthesis of 2,3,7,8-tetrathiaspiro[4.4]nonane (1), a key synthetic intermediate of 2,2-bis(mercaptomethyl)propane-1,3-dithiol [tetramercaptan pentaerythritol]. Starting...

Descripción completa

Detalles Bibliográficos
Autores principales: Kondo, Masaru, Wathsala, Hettiarachchige Dona Piyumi, Ishikawa, Kazunori, Yamashita, Daisuke, Miyazaki, Takeshi, Ohno, Yoji, Sasai, Hiroaki, Washio, Takashi, Takizawa, Shinobu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10343712/
https://www.ncbi.nlm.nih.gov/pubmed/37446842
http://dx.doi.org/10.3390/molecules28135180
_version_ 1785072802175385600
author Kondo, Masaru
Wathsala, Hettiarachchige Dona Piyumi
Ishikawa, Kazunori
Yamashita, Daisuke
Miyazaki, Takeshi
Ohno, Yoji
Sasai, Hiroaki
Washio, Takashi
Takizawa, Shinobu
author_facet Kondo, Masaru
Wathsala, Hettiarachchige Dona Piyumi
Ishikawa, Kazunori
Yamashita, Daisuke
Miyazaki, Takeshi
Ohno, Yoji
Sasai, Hiroaki
Washio, Takashi
Takizawa, Shinobu
author_sort Kondo, Masaru
collection PubMed
description Bayesian optimization (BO)-assisted screening was applied to identify improved reaction conditions toward a hundred-gram scale-up synthesis of 2,3,7,8-tetrathiaspiro[4.4]nonane (1), a key synthetic intermediate of 2,2-bis(mercaptomethyl)propane-1,3-dithiol [tetramercaptan pentaerythritol]. Starting from the initial training set (ITS) consisting of six trials sampled by random screening for BO, suitable parameters were predicted (78% conversion yield of spiro-dithiolane 1) within seven experiments. Moreover, BO-assisted screening with the ITS selected by Latin hypercube sampling (LHS) further improved the yield of 1 to 89% within the eight trials. The established conditions were confirmed to be satisfactory for a hundred grams scale-up synthesis of 1.
format Online
Article
Text
id pubmed-10343712
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-103437122023-07-14 Bayesian Optimization-Assisted Screening to Identify Improved Reaction Conditions for Spiro-Dithiolane Synthesis Kondo, Masaru Wathsala, Hettiarachchige Dona Piyumi Ishikawa, Kazunori Yamashita, Daisuke Miyazaki, Takeshi Ohno, Yoji Sasai, Hiroaki Washio, Takashi Takizawa, Shinobu Molecules Article Bayesian optimization (BO)-assisted screening was applied to identify improved reaction conditions toward a hundred-gram scale-up synthesis of 2,3,7,8-tetrathiaspiro[4.4]nonane (1), a key synthetic intermediate of 2,2-bis(mercaptomethyl)propane-1,3-dithiol [tetramercaptan pentaerythritol]. Starting from the initial training set (ITS) consisting of six trials sampled by random screening for BO, suitable parameters were predicted (78% conversion yield of spiro-dithiolane 1) within seven experiments. Moreover, BO-assisted screening with the ITS selected by Latin hypercube sampling (LHS) further improved the yield of 1 to 89% within the eight trials. The established conditions were confirmed to be satisfactory for a hundred grams scale-up synthesis of 1. MDPI 2023-07-03 /pmc/articles/PMC10343712/ /pubmed/37446842 http://dx.doi.org/10.3390/molecules28135180 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Kondo, Masaru
Wathsala, Hettiarachchige Dona Piyumi
Ishikawa, Kazunori
Yamashita, Daisuke
Miyazaki, Takeshi
Ohno, Yoji
Sasai, Hiroaki
Washio, Takashi
Takizawa, Shinobu
Bayesian Optimization-Assisted Screening to Identify Improved Reaction Conditions for Spiro-Dithiolane Synthesis
title Bayesian Optimization-Assisted Screening to Identify Improved Reaction Conditions for Spiro-Dithiolane Synthesis
title_full Bayesian Optimization-Assisted Screening to Identify Improved Reaction Conditions for Spiro-Dithiolane Synthesis
title_fullStr Bayesian Optimization-Assisted Screening to Identify Improved Reaction Conditions for Spiro-Dithiolane Synthesis
title_full_unstemmed Bayesian Optimization-Assisted Screening to Identify Improved Reaction Conditions for Spiro-Dithiolane Synthesis
title_short Bayesian Optimization-Assisted Screening to Identify Improved Reaction Conditions for Spiro-Dithiolane Synthesis
title_sort bayesian optimization-assisted screening to identify improved reaction conditions for spiro-dithiolane synthesis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10343712/
https://www.ncbi.nlm.nih.gov/pubmed/37446842
http://dx.doi.org/10.3390/molecules28135180
work_keys_str_mv AT kondomasaru bayesianoptimizationassistedscreeningtoidentifyimprovedreactionconditionsforspirodithiolanesynthesis
AT wathsalahettiarachchigedonapiyumi bayesianoptimizationassistedscreeningtoidentifyimprovedreactionconditionsforspirodithiolanesynthesis
AT ishikawakazunori bayesianoptimizationassistedscreeningtoidentifyimprovedreactionconditionsforspirodithiolanesynthesis
AT yamashitadaisuke bayesianoptimizationassistedscreeningtoidentifyimprovedreactionconditionsforspirodithiolanesynthesis
AT miyazakitakeshi bayesianoptimizationassistedscreeningtoidentifyimprovedreactionconditionsforspirodithiolanesynthesis
AT ohnoyoji bayesianoptimizationassistedscreeningtoidentifyimprovedreactionconditionsforspirodithiolanesynthesis
AT sasaihiroaki bayesianoptimizationassistedscreeningtoidentifyimprovedreactionconditionsforspirodithiolanesynthesis
AT washiotakashi bayesianoptimizationassistedscreeningtoidentifyimprovedreactionconditionsforspirodithiolanesynthesis
AT takizawashinobu bayesianoptimizationassistedscreeningtoidentifyimprovedreactionconditionsforspirodithiolanesynthesis

Ejemplares similares