Sodium hydride/hexamethylphosphoric triamide: a new and efficient reagent towards the synthesis of protected 1,2-and 5,6-enopyranosides

Authors
Khan, KM Perveen, S Ali Shah, STG Shekhani, MS Voelter, W
Citation
Km. Khan et al., Sodium hydride/hexamethylphosphoric triamide: a new and efficient reagent towards the synthesis of protected 1,2-and 5,6-enopyranosides, NEW J CHEM, 25(7), 2001, pp. 896-898
Citations number
48
Categorie Soggetti
Chemistry
Journal title
NEW JOURNAL OF CHEMISTRY
ISSN journal
11440546 → ACNP
Volume
25
Issue
7
Year of publication
2001
Pages
896 - 898
Database
ISI
SICI code
1144-0546(2001)25:7<896:SHTANA>2.0.ZU;2-Q
Abstract
A new method for the elimination of hydrogen halides and p-toluenesulfonic acid from sugar moieties using sodium hydride (NaH) in hexamethylphosphoric triamide (HMPA) at room temperature is reported. NaH/HMPA has several adva ntages compared to NaH/DMF: elimination products are produced in high yield s even from sterically hindered starting materials, and not only from halid es, but also tosylates.