Synthesis of five and six membered aminocyclitols: stereoselective michael and henry reaction approach with D-glucose derived alpha,beta-unsaturated ester

TitleSynthesis of five and six membered aminocyclitols: stereoselective michael and henry reaction approach with D-glucose derived alpha,beta-unsaturated ester
Publication TypeJournal Article
Year of Publication2008
AuthorsChakraborty, C, Vyavahare, VP, Puranik, VG, Dhavale, DD
JournalTetrahedron
Volume64
Issue40
Pagination9574-9580
Date PublishedSEP
Type of ArticleArticle
ISSN0040-4020
Keywordsaminocyclitols, carbohydrates, Henry reaction, Michael addition, nitroinositol
Abstract

The stereoselective intermolecular Michael addition of nitromethane to D-glucose derived alpha,beta-unSaturated ester 7 afforded L-ido-configurated nitroester 8 as the only product that on reduction of the ester functionality, cleavage of 1,2-acetonide and the intramolecular Henry reaction afforded exclusively muco-nitroinositol 9. While reduction of the ester functionality in 8, deprotection of 1,2-acetonide, oxidative cleavage with NaIO(4) and the intrarnolecular Henry reaction afforded nitrocyclopentitol 13. Nitrocyclitols 9 and 13 were converted to the hydroxyethyl substituted aminocyclohexitol 5 and aminocyclopentitol 6, respectively. (C) 2008 Elsevier Ltd. All rights reserved.

DOI10.1016/j.tet.2008.07.049
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.645

Divison category: 
Center for Material Characterization (CMC)
Physical and Materials Chemistry