Preparation of 2,5-anhydrohexitols - (Part II). Intramolecular nucleophilic substitution of cyclic sulfates

Authors
van Delft, FL Valentijn, ARPM van der Marel, GA van Boom, JH
Citation
Fl. Van Delft et al., Preparation of 2,5-anhydrohexitols - (Part II). Intramolecular nucleophilic substitution of cyclic sulfates, J CARB CHEM, 18(2), 1999, pp. 191-207
Citations number
27
Categorie Soggetti
Chemistry & Analysis
Journal title
JOURNAL OF CARBOHYDRATE CHEMISTRY
ISSN journal
07328303 → ACNP
Volume
18
Issue
2
Year of publication
1999
Pages
191 - 207
Database
ISI
SICI code
0732-8303(1999)18:2<191:PO2-(I>2.0.ZU;2-9
Abstract
The 2-O-acetyl-3,4-di-O-benzyl-5,6-O-cyclic sulfates 5, 16 and 25, derived from D-arabinose, D-ribose and D-xylose, respectively, are useful precursor s in the synthesis of 2,5-anhydrohexitols. 5-Exo-tet cyclization of compoun ds 5, 16, and 25 under the influence of base leads to the predominant or ex clusive formation of the corresponding tetrahydrofuran derivatives.