Synthesis of 1,6-Anhydro-2,3-di-O-farnesyl-5-O-([{phosphonomethyl}phosphinyl]methyl)-α-d-galactofuranose: A Zaragozic Acid-Presqualene Pyrophosphate Hybrid
- 1 August 1995
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 14 (6) , 737-749
- https://doi.org/10.1080/07328309508005373
Abstract
A multi-step synthesis of a new potential inhibitor (i.e., compound 2) of squalene synthase is described, starting from D-galactose. The title compound is a hybrid of presqualene pyrophopshate and the recently discovered zaragozic acids, which are picomolar competitive inhibitors of the enzyme squalene synthase.Keywords
This publication has 20 references indexed in Scilit:
- Total Synthesis of Zaragozic Acid A/Squalestatin S1Angewandte Chemie International Edition in English, 1994
- Synthesis of (+)-Zaragozic Acid CJournal of the American Chemical Society, 1994
- A novel approach towards the synthesis of pyrophosphate analogues of farnesyl pyrophosphateRecueil des Travaux Chimiques des Pays-Bas, 1994
- Facile Preparation of 1,6-Anhydrohexoses using Solvent Effects and a Catalytic Amount of a Lewis Acid.Acta Chemica Scandinavica, 1994
- A synthetic approach to squalestatin 1Journal of the Chemical Society, Chemical Communications, 1993
- Zaragozic acid A, a potent inhibitor of squalene synthase: initial chemistry and absolute stereochemistryThe Journal of Organic Chemistry, 1992
- An Expeditious Synthesis of Pyrophosphate Analogues of Farnesyl Pyrophosphate Using the Phosphonylating Agent Methyl MethylphosphonomorpholidateSynlett, 1991
- Armed and disarmed n-pentenyl glycosides in saccharide couplings leading to oligosaccharidesJournal of the American Chemical Society, 1988
- A Simple Regioselective Partial Hydrolysis of Di-O-isopropylidene Monosaccharides with Copper(II) IonBulletin of the Chemical Society of Japan, 1981
- THE FIFTH PENTA-ACETATE OF GALACTOSE, ITS ALCOHOLATE AND ALDEHYDROLJournal of the American Chemical Society, 1930