Fluorous Technologies - On-line catalog

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Protecting groups and tags

Scavengers - nucleophilic

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Protecting groups and

tags

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CONTACT FTI

♦ Boc-ON

♦ Silanes

♦ PMB OH

♦ t-Butanol

♦ Cbz-Osu

♦ Thiol

♦ Benzyl alcohol

♦ FluoMar

♦ Oxybenzaldehyde

♦ Fmoc

♦ Trityl Chlorides

♦ Trityl Alcohols

♦ Thiophenol

Fluorous tags are perfluoroalkyl modified versions of traditional protecting groups familiar to synthetic organic chemists. Conceptually they are very similar to solid phase tags, but fluorous tags and fluorous tagged substrates are soluble in most organic solvents, such as DMF, THF, CH2Cl2, etc. This provides some distinct advantages over solid phase tagging strategies including solution phase kinetics, complete control of reaction stoichiometry, and the ability to monitor reactions easily using traditional analytical techniques, including TLC, NMR, GC, LC/MS, and IR. The fluorous tagged materials are easily separated from non-tagged components by F-SPE. Fluorous tags have been used in a variety of total, parallel, and mixture syntheses (1-3).

1. Zhang, W. “Fluorous Protecting Groups and Tags” in Handbook of Fluorous Chemistry Gladysz, J. A.; Curran, D. P.; Horvath, I. T. Eds. Wiley-VCH, 2004, pp222-2362.

2. Zhang, W. “Fluorous Tagging Strategy for Solution-Phase Synthesis of Small Molecules, Peptides and Oligosaccharides” Curr. Opin. Drug Disov. Develop. 2004, 7, 784-797.

3. Curran, D. P. In Stimulating Concepts in Chemistry; Stoddard, F., Reinhoudt, D., Shibasaki, M., Eds.; Wiley-VCH: New York, 2000, p 25-37.

Boc-ON

F-Boc-ON is the fluorous equivalent of 2-(t-butoxycarbonyloxyimino)-2-phenylacetonitrile (BOC-ON) primarily used in the protection of amines. Analogous to conventional Boc, the fluorous Boc group is acid labile, but stable to a wide range of basic and nucleophilic conditions. F017003, the C8F17 analog of F-Boc has appropriate fluorine content for the tagging of diverse organic molecules and is recommended for natural product or medicinal chemistry synthesis in combination with fluorous solid phase extraction. The other F-Boc homologs are useful in fluorous HPLC and fluorous mixture synthesis.

Luo, Z. Y.; Williams, J.; Read, R. W.; Curran, D.P. J.Org Chem. 2001, 66, 4261.
Zhang, W. ‘Fluorous Protecting Groups and Tags’ in Handbook of Fluorous Chemistry, Gladysz, J. A.; Curran, D. P.; Horvath, I. T. Eds. Wiley-VCH, 2004, pp 222-236.
Curran, D. P. Synlett 2001, 1488. Curran, D. P. ‘Separations with Fluorous Silica Gel and Related Materials’, in Handbook of Fluorous Chemistry; Wiley-VCH: Weinheim, 2004; pp 101-127.
FTI Application Note "Fluorous Solid Phase Extraction"
Zhang, W. Arkivoc 2004 (i), 101-109.
Zhang, W. Tempest, P. “Highly Efficient Microwave-Assisted Fluorous Ugi and Post-Condensation Reactions for Benzimidazoles and Quinoxalinones” Tetrahedron Lett. 2004, 45, 6757-6760.
7) Sreeman K. Mamidyala and Steven M. Firestine “Fluorous synthesis of minor groove binding agents related to distamycin” Tetrahedron Lett. 2006, 47, 7431-7434.

Rf	NAME/CAS#	PROPERTIES	CATALOG#	QTY	PRICE
C₃F₇	2-[2-(1H,1H,2H,2H-Perfluoropentyl) isopropoxycarbonyloxyimino]-2-phenylacetonitrile	C₁₇H₁₅F₇N₂O₃	F007003-0002	2g	$88.50
		FW: 428.34	F007003-0010	10g	$365.50
			F007003-0025	25g	$785.50
			F007003-0100	100g	$2,163.00

C₄F₉	2-[2-(1H,1H,2H,2H-Perfluorohexyl) isopropoxycarbonyloxyimino]-2-phenylacetonitrile	C₁₈H₁₅F₉N₂O₃	F009003-0002	2g	$66.00
		FW: 478.35	F009003-0010	10g	$278.00
			F009003-0025	25g	$592.50
			F009003-0100	100g	$1,648.00

C₆F₁₃	2-[2-(1H,1H,2H,2H-Perfluorooctyl) isopropoxycarbonyloxyimino]-2-phenylacetonitrile	C₂₀H₁₅F₁₃N₂O₃	F013003-0002	2g	$65.00
		FW: 578.37	F013003-0010	10g	$273.00
			F013003-0025	25g	$579.50
			F013003-0100	100g	$1,596.50

(CF₂)₄CF(CF₃)₂	2-[2-(1H,1H,2H,2H-Perfluoro-7-methyloctyl) isopropoxycarbonyloxyimino]-2-phenylacetonitrile	C₂₁H₁₅F₁₅N₂O₃	F015003-0002	2g	$153.50
		FW: 628.38	F015003-0010	10g	$638.50
			F015003-0025	25g	$1,352.00
			F015003-0100	100g	$3,811.00

C₈F₁₇	2-[2(1H,1H,2H,2H-Perfluorodecyl) isopropoxycarbonyloxyimino]-2-phenylacetonitrile 3350716-42-6	C₂₂H₁₅F₁₇N₂O₃	F017003-0002	2g	$61.00
		FW: 678.39	F017003-0010	10g	$252.50
			F017003-0025	25g	$541.00
			F017003-0100	100g	$1,493.50

(CF₂)₆CF(CF₃)₂	2-[2-(1H,1H,2H,2H-Perfluoro-9-methyldecyl) isopropoxycarbonyloxyimino]-2-phenylacetonitrile	C₂₃H₁₅F₁₉N₂O₃	F019003-0002	2g	$80.50
		FW: 728.40	F019003-0010	10g	$335.00
			F019003-0025	25g	$721.00
			F019003-0100	100g	$2,008.50

C₁₀F₂₁	2-[2-(1H,1H,2H,2H-Perfluorododecyl) isopropoxycarbonyloxyimino]-2-phenylacetonitrile	C₂₄H₁₅F₂₁N₂O₃	F021003-0002	2g	$72.00
		FW: 778.41	F021003-0010	10g	$304.00
			F021003-0025	25g	$644.00
			F021003-0100	100g	$1,802.50

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