Alternative Syntheses of L-(-)-Oleandrose from L-Rhamnose1Preparation of Glycals
- 1 September 1992
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 22 (17), 2459-2477
- https://doi.org/10.1080/00397919208021642
Abstract
L-Rhamnal (2) is prepared from L-rhamnose (3) by use of an improved generalized Fischer-Zach reaction. L-Rhamnal (2) is then converted to L-(-)-oleandrose (1) by stannylene mediated selective methylation and effective hydration. Benzyl α-L-oleandrose (12) is prepared by selective methylation and deoxygenation of L-rhamnose (3).Keywords
This publication has 35 references indexed in Scilit:
- An Efficient Three-Step Synthesis of L-(-)-Oleandrose from (S)-(-)-Methyl LactateSynlett, 1990
- The total synthesis of avermectin A1aJournal of the American Chemical Society, 1989
- Selective deoxygenation via regioselective thioacylation of non-protected glycopyranosides by the dibutyltin oxide method.CHEMICAL & PHARMACEUTICAL BULLETIN, 1987
- Biosynthese von Herzglykosiden: Nachweis von nukleotidgebundenen 2,6-Didesoxy-3-O-Methylhexosen in Blättern von Nerium oleanderPlanta Medica, 1984
- Regioselective monoacylation of some glycopyranosides via cyclic tin intermediates.CHEMICAL & PHARMACEUTICAL BULLETIN, 1983
- Acid-catalyzed and enzymatic hydrolysis of trans- and cis-2-methyl-3,4-epoxytetrahydropyranJournal of the Chemical Society, Perkin Transactions 1, 1983
- Avermectins. Structure determinationJournal of the American Chemical Society, 1981
- An alternative route to furanoid and pyranoid glycalsJournal of the Chemical Society, Perkin Transactions 1, 1978
- A method for the preparation of furanoid glycalsJournal of the Chemical Society, Chemical Communications, 1977
- Oleandomycin (PA-105). II.1,2 Chemical Characterization (I)Journal of the American Chemical Society, 1958