Allyl C-Glycosidation of Glycals Mediated by 2,3-Dichloro-5,6-dicyano-p-benzoquinone (DDQ)
- 1 December 1993
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 22 (12) , 2013-2016
- https://doi.org/10.1246/cl.1993.2013
Abstract
A novel and highly stereoselective method for the synthesis of allyl C-glycosides bearing C2-C3 unsaturation has been developed using glycal acetate, allyltrimethylsilane and 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) as a neutral activator.Keywords
This publication has 9 references indexed in Scilit:
- Assignment of anomeric configuration of C-glycopyranosides and C-glycofuranosides. A proton, carbon-13, and nuclear Overhauser enhancement spectrometric studyThe Journal of Organic Chemistry, 1993
- Synthesis of C-glycosyl compounds from 3,4,6-tri-O-acetyl-1,5-anhydro-d-arabino-hex-1-enitol and allyltrimethylsilane and bis(trimethylsilyl)acetyleneCarbohydrate Research, 1987
- A concise and stereoselective route to the predominant stereochemical pattern of the tetrahydropyranoid antibiotics: an application to indanomycinJournal of the American Chemical Society, 1987
- Synthesis of C-disaccharidesThe Journal of Organic Chemistry, 1987
- Synthesis of a marine polyether toxin, okadaic acid (2) — synthesis of segment bTetrahedron, 1987
- Model studies directed toward the avermectins: A route to the spiroketal subunitTetrahedron Letters, 1987
- 1 The Chemistry and Biochemistry of C-Nucleosides and C-ArylglycosidesPublished by Elsevier ,1985
- On the addition of allyltrimethylsilane to glycal acetatesThe Journal of Organic Chemistry, 1982
- Highly stereoselective approaches to .alpha.- and .beta.-C-glycopyranosidesJournal of the American Chemical Society, 1982