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To view the APRIL 2004 Newsletter, please click here.

FTI's Product Selection Tool to the Rescue!

In an effort to make your fluorous product selection easier, FTI has released a series of product selection tools. Simply select the functionality that you are interested in synthesizing and our convenient hyperlinked webpage will guide you to the fluorous product best suited for the desired transformation. If you have specific product questions, please contact Kris Mikulan, our technical support specialist by clicking here.

Key Licensed Patent Issues for Fluorous Technologies

US Patent 6,673,539 entitled "Fluorous Tagging Compounds and Methods of Use Thereof", which FTI has exclusively licensed from the University of Pittsburgh, issued recently. The patent broadly covers the use of fluorous tags and separation techniques in conjunction with solid support chemistry. This tagging strategy has recently been demonstrated in peptide and oligomer synthesis and the company is actively seeking partners to further explore commercial applications in these areas.  To see the entire press release, please click here.

Fluorous Scavengers Outperform Solid-Bound Scavengers

Polymer-bound scavenging has become a popular synthetic technique for the removal of excess reagents. Polymer scavenging, however, can be slow due to the heterogenous reaction conditions and a large amount (3-5 equivalents or more) of the solid-supported scavenger is commonly used. Fluorous scavengers react more efficiently than solid-supported scavengers due to the complete solution –phase nature of the chemistry. In the scavenging reaction shown below, N-phenylpiperazine was reacted with isatoic anhydride, polymer supported isatoic anhydride, and fluorous isatoic anhydride. After 60 min., the fluorous isatoic anhydride reaction indicated <10% of amine remained, while the polymer-supported example using 1.5 equiv. still had 84% remaining. Increasing the amount used to 3.0 equiv still leaves 44% of the amine remaining after 60 min. demonstrating the superior reactivity of the fluorous scavenger. In an another example comparing fluorous thiols to silica supported thiols, the fluorous scavenger was found to be about 10 times more efficient, once again due to the complete solution phase chemistry involved. In each case the desired product can be convienently purified using flurous solid phase extraction (F-SPE).   FTI has recently updated its entire scavenging website.  Please click here to see the recent developments in F-scavenging.

FTI at CHI's High-Throughput Purification Forum on Feb. 26, 2004

Prof. Dennis Curran, founder of Fluorous Technologies, will be the keynote speaker at CHI's one-day High-Throughput Purification Forum.  This forum will follow the three day Advancing Library Design and Organic Synthesis Conference In La Jolla, CA from Feb. 23-25th, 2004 .

As a guest of Fluorous Technologies, you are entitled to a $100 discount on a commercial registration and $50 discount on an academic registration!  To register, click here ( please note: you must use this link to receive the discount if registering on-line ) or call Cambridge Healthtech Institute directly at 617-630-1300 and ask for Registration.  Be sure to mention your priority code: LDSFL in order to receive your discount.

Cutting Edge Fluorous Chemistry

Fluorous Silyl Protecting Group Eases Separation of Oligosaccharides:

In a recent publication, Leonardo Manzoni of the Institute of Molecular Science and Technologies, Milan, Italy, showed that the use of a fluorous tag as a protecting group at the anomeric position of a glycosyl acceptor allowed for rapid separation of disaccharides by fluorous solid-phase extraction (F-SPE). The disaccharide was obtained in 36% overall yield from 4 (four steps) without the need for normal or reversed phase silica gel chromatography. Each synthetic intermediate could be easily purified by F-SPE and characterized by NMR, mass spectroscopy (MALDI-TOF), and TLC on standard silica gel plates. Manzoni commented, "This is a major advantage over classical solid-phase synthesis conditions, and allows rapid optimization of the reaction conditions for each synthetic step. Compared to reaction of PEG-supported carbohydrates, the fluorous tag strategy has the advantage of allowing the use of silica gel TLC to monitor the reaction process. Furthermore, the NMR signals originating from the fluorous tag do not interfere with the carbohydrate region, thus allowing an easy characterization of the tagged compounds. The optimization of the glycosidation conditions, such as the study of new silyl fluorous tags, and further applications to the synthesis of several carbohydrates and glyconjugates are now in progress." Manzoni, Leonardo. "Rapid synthesis of oligosaccharides using an anomeric fluorous silyl protecting group." ChemComm (The Royal Society of Chemistry), 2003, 2930-2931.

Concept of oligosaccharide synthesis using a fluorous tag at

the anomeric position of the glycosyl acceptor.

Reaction Scheme: a) tert-Butyl-phenyl-1H,1H,2H,2H-heptadecafluoro

decyloxysilylbromide, imidazole, DMAP, DCM, 85%; b) MeONa, MeOH,

quant.; c) benzaldehyde dimethylacetal, CSA, CH3CN, 75% after 2 cycles;

d) 7, TMSOTf, DCM, 78% after 2 cycles; e) TBAF, THF, 62%.

Fluorous Technologies, Inc. (FTI) is a chemical technology company dedicated to the development and commercialization of fluorous products focused at the life science market. The company uses patented technology to solve synthesis and separation problems spanning the entire drug discovery and development process. FTI further leverages its enabling technology through service contracts, licenses, and collaborations.

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