Asymmetric synthesis of inositol derivatives

TitleAsymmetric synthesis of inositol derivatives
Publication TypeJournal Article
Year of Publication2024
AuthorsPatil, NT, Sarkar, N, S. Mysore, S, Gonnade, RG
JournalTetrahedron
Volume162
Pagination134113
Date PublishedAUG
Type of ArticleArticle
ISSN0040-4020
KeywordsAsymmetric synthesis, Carbohydrate, Cyclitol, Inositol, Natural product
Abstract

Both the enantiomers of racemic 4- O -tosyl-6- O -benzyl- myo -inositol-1,3,5-orthoformate ( 2 ) were isolated by preferential crystallization and used to synthesize several enantiomeric myo -inositol derivatives - natural ononitol, natural laminitol, precursors for myo -inositol phosphates and an oxabicyclo [2.2.1] heptane derivative. This work demonstrates the potential of the enantiomeric tosylates D2 and L2 to serve as versatile starting materials for the absolute asymmetric synthesis of inositol derivatives and other natural products from symmetric myo -inositol since no optically active molecular entity was required for the resolution of 2.

DOI10.1016/j.tet.2024.134113
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.1

Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry
Database: 
Web of Science (WoS)

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