Facile Oxidative Cleavage of 4-O-Benzyl Ethers with Dichlorodicyanoquinone in Rhamno- and Mannopyranosides
- 22 March 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 72 (9) , 3581-3584
- https://doi.org/10.1021/jo062411p
Abstract
On exposure to dichlorodicyanoquinone in wet dichloromethane at room temperature, equatorial 4-O-benzyl ethers are removed with moderate selectivity in the presence of other benzyl ethers in glycopyranosides and glycothiopyranosides.Keywords
This publication has 27 references indexed in Scilit:
- Stereocontrolled Synthesis of the d- and l-glycero-β-d-manno-Heptopyranosides and Their 6-Deoxy Analogues. Synthesis of Methyl α-l-Rhamno-pyranosyl-(1→3)-d-glycero-β-d-manno-heptopyranosyl- (1→3)-6-deoxy-glycero-β-d-manno-heptopyranosyl-(1→4)-α-l- rhamno-pyranoside, a Tetrasaccharide Subunit of the Lipopolysaccharide from Plesimonas shigelloidesJournal of the American Chemical Society, 2006
- Enhanced Diastereoselectivity in β-Mannopyranosylation through the Use of Sterically Minimal Propargyl Ether Protecting GroupsThe Journal of Organic Chemistry, 2006
- C3 Chirality in Polymerization Catalysis: A Highly Active Dicationic Scandium(III) Catalyst for the Isoselective Polymerization of 1-HexeneAngewandte Chemie International Edition in English, 2005
- Direct Chemical Synthesis of the β-Mannans: Linear and Block Syntheses of the Alternating β-(1→3)-β-(1→4)-Mannan Common to Rhodotorula glutinis, Rhodotorula mucilaginosa, and Leptospira biflexaJournal of the American Chemical Society, 2004
- Direct Chemical Synthesis of the β-d-Mannans: The β-(1→2) and β-(1→4) SeriesJournal of the American Chemical Society, 2004
- Benzylidene Acetal Fragmentation Route to 6-Deoxy Sugars: Direct Reductive Cleavage in the Presence of Ether Protecting Groups, Permitting the Efficient, Highly Stereocontrolled Synthesis of β-d-Rhamnosides from d-Mannosyl Glycosyl Donors. Total Synthesis of α-d-Gal-(1→3)-α-d-Rha-(1→3)- β-d-Rha-(1→4)-β-d-Glu-OMe, the Repeating Unit of the Antigenic Lipopolysaccharide from Escherichia hermannii ATCC 33650 and 33652Journal of the American Chemical Society, 2004
- A Simple Method for the Selective Deprotection of p-Methoxybenzyl Ethers by Cerium(III) Chloride Heptahydrate and Sodium IodideThe Journal of Organic Chemistry, 1999
- Total Synthesis and Absolute Configuration of Polycavernoside AJournal of the American Chemical Society, 1998
- Total synthesis of (-)-hikizimycin employing the strategy of two-directional chain synthesisJournal of the American Chemical Society, 1992
- Catalytic cyclophanes. 4. Supramolecular catalysis of benzoin condensations by a thiazolium cyclophaneJournal of the American Chemical Society, 1989