SYNTHESIS, CHARACTERIZATION, IN SILICO OPTIMIZATION, AND CONFORMATIONAL STUDIES OF METHYL 4-O-PIVALOYL-α-L-RHAMNOPYRANOSIDES

Main Article Content

Mohammed Mahbubul Matin, PhD, Postdoc
http://orcid.org/0000-0003-4965-2280
Mohammad Ibrahim
http://orcid.org/0000-0001-7360-7776
Tasnim Rahman Anisa, Ms
http://orcid.org/0000-0001-9377-4563
Md. Rezaur Rahman, PhD
http://orcid.org/0000-0002-7151-0687

Abstract

Considering promising biological activities of natural and synthetic rhamnopyranoside esters, we have synthesized several methyl 4-O-pivaloyl-α-L-rhamnopyranosides via selective 2,3-O-acetonide protection of methyl α-L-rhamnopyranoside (4) followed by C-4 pivaloylation, and deprotection. The synthesized 4-O-pivaloate 7 and its 2,3-di-O-esters 8a-e are characterized by spectroscopy and are optimized by using density functional theory (DFT). The free energy and bond angles thus calculated are used to establish the probable conformation(s). The 2,3-O-acetonide protected rhamnopyranosides 5-6 are found to be slightly distorted from the regular 1C4 conformation, and exist between the chair and twist-boat (skew) conformation while other pivaloyl esters 7-8a-e exist in regular 1C4 chair conformation.

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How to Cite
Matin, M. M., Ibrahim, M., Anisa, T. R., & Rahman, M. R. (2022). SYNTHESIS, CHARACTERIZATION, IN SILICO OPTIMIZATION, AND CONFORMATIONAL STUDIES OF METHYL 4-O-PIVALOYL-α-L-RHAMNOPYRANOSIDES. Malaysian Journal of Science, 41(1), 91–105. https://doi.org/10.22452/mjs.vol41no1.6
Section
Original Articles
Author Biographies

Mohammed Mahbubul Matin, PhD, Postdoc, University of Chittagong

Department of Chemistry

Professor

Mohammad Ibrahim, Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry, Faculty of Science, University of Chittagong, Chattogram, 4331

Principal

Tasnim Rahman Anisa, Ms, Bioorganic and Medicinal Chemistry Laboratory, Department of Chemistry, Faculty of Science, University of Chittagong, Chattogram, 4331

Department of Chemistry

Researcher

Md. Rezaur Rahman, PhD, Department of Chemical Engineering and Energy Sustainability, Faculty of Engineering, Universiti Malaysia Sarawak, Jalan Datuk Mohammad Musa, Kota Samarahan, 94300

Department of Chemical Engineering and Energy Sustainability

Senior Lecturer

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