Synthesis of a β-(1→3)-d-Rhamnotetraose by a One-Pot, Multiple Radical Fragmentation
Open Access
- 17 August 2006
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 8 (19) , 4327-4330
- https://doi.org/10.1021/ol061706m
Abstract
A naturally occurring β-(1→3)-d-rhamnotetraose has been constructed under conditions of sequential β-selective mannosylation controlled by the 4,6-O-[1-cyano-2-(2-iodophenyl)-ethylidene] protecting group. The route is concise, proceeding through a late-stage radical deoxygenation that successfully uncovers all four deoxy subunits at once.Keywords
This publication has 59 references indexed in Scilit:
- 4,6-O-[1-Cyano-2-(2-iodophenyl)ethylidene] Acetals. Improved Second-Generation Acetals for the Stereoselective Formation of β-d-Mannopyranosides and Regioselective Reductive Radical Fragmentation to β-d-Rhamnopyranosides. Scope and LimitationsThe Journal of Organic Chemistry, 2006
- 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
- Chemical Synthesis of Normal and Transformed PSA GlycopeptidesJournal of the American Chemical Society, 2003
- Regiocontrol in the Oxidative Radical Fragmentation of Benzilidene Acetals and Its Mechanistic ImplicationsThe Journal of Organic Chemistry, 2003
- Toward Fully Synthetic N‐Linked GlycoproteinsAngewandte Chemie International Edition in English, 2003
- Direct Synthesis of β-Mannans. A Hexameric [→3)-β-d-Man-(1→4)-β-d-Man-(1]3 Subunit of the Antigenic Polysaccharides from Leptospira biflexa and the Octameric (1→2)-Linked β-d-Mannan of the Candida albicans Phospholipomannan. X-ray Crystal Structure of a Protected TetramerJournal of the American Chemical Society, 2001
- Recent advances in the construction of β-D-mannose and β-D-mannosamine linkagesJournal of the Chemical Society, Perkin Transactions 1, 2000
- Ring opening of 2,3-, 3,4-, and 4,6-O-benzylidene acetals of pyranosides by photobromination with bromotrichloromethaneJournal of the Chemical Society, Chemical Communications, 1988
- Stereoelectronic effects in hydrogen atom abstraction from substituted 1,3-dioxanesJournal of the American Chemical Society, 1981