2-deoxy-2-fluoro synthesis

Simple one-pot synthesis of different 1-0-glycosylboranophosphate diesters (65), the stable analogues of 1-0-glycosylphosphates based on the anomeric H-phosphonate of a-L-rhamnopyranose as common precursor, has been reported. Various phosphodisaccharides, structural analogues of phosphate (66) including deoxy, fluoro and aminodeoxy disaccharide phosphates e.g. (67) have been synthesized. These phosphodisaccharides were tested as acceptor sub-strate/putative inhibitors for the Leishmania-a-D-mannosylphosphate transferase. [Pg.114]

The 5-deoxy-fluoro-sugar derivatives (15) and (16) have been synthesised from D-glucose for incorporation into potential chemotherapeutic nucleosides. Improvements to Ogawa s method for the synthesis of 2-deoxy- -glycosides, involving addition of arylsulphenyl esters of the desired aglycon to glycals, with... [Pg.130]

Acetalated myo-inositol derivatives have been converted by standard reactions into intermediates required for the total synthesis of sugarotoxin and some of its analogues, which are 6-0-acyl derivatives of myo-inositol.Quebrachitol reacts with DAST to a deoxy-fluoro derivative which, on demethylation, gave the fluoro-inositol (54), a cellular replication inhibitor.Deoxy-fluoro-myo-inositols have been prepared, and their behaviour as substrates for phosphatidyl-inositol synthetase has been reported. 2-C-fluoromethyl-myo-inositol (55) has been prepared conventionally from an exocyclic oxiran precursor. [Pg.186]

In 2003 LJngstrOm and Samuelsson described the synthesis of a radiopharmaceutical for PET (positron emission tomography) using a microwave-assisted Stille reaction [25]. l-(2 -Deoxy-2 -fluoro- 6-D-arabinofuranosyl)-... [Pg.159]

Stuyver LJ, McBrayer TR, Tharnish PM, Clark J, Hollecker L, Lostia S, Nachman T, Grier J, Bennett MA, Xie MY, Schinazi RF, Morrey JD, Inlander JL, Furman PA, Otto MJ (2006a) Inhibition of hepatitis C replicon RNA synthesis by beta-D-2 -deoxy-2 -fluoro-2 -C-methylcytidine a specific inhibitor of hepatitis C virus replication, Antivir Chem Chemother 17 79-87... [Pg.50]

Considerable interest has been focused on the efficient and rapid synthesis of 2-deoxy-2-[ F]fluoro-D-gIucose, a popular imaging agent for positron-emission tomography (see Section III, 1). However, introduction of a fluorine atom at C-2 by nucleophilic displacement is generally not easy on account of the weak nucleophilic character of the fluoride ion. One possible... [Pg.121]

Syntheses of 3-deoxy-3-fluoro sugars are described next. A rapid synthesis aimed at 3-deoxy-3-[ F]fluoro-D-glucose ( F-3DFG) was developed. ... [Pg.133]

In 1969, Adamson, Foster, and others - reported the synthesis of 2-deoxy-2-fluoro sugars by addition ofCFjOF (in CFCI3, — 80°) to 3,4,6-tri-O-acetyl-l,5-anhydro-2-deoxy-D-flra/)/>zo-hex-l-enitol (61 3,4,6-tri-O-acetyl-D-glucal). The reagent fluorinates 61 electrophilically - °° at C-2, to afford c/v-addition products trifluoromethyl 3,4,6-tri-C)-acetyl-2-deoxy-2-... [Pg.170]

Deoxy-3-fluoro-D-glucose (25%) and -mannose (40%) were prepared from 2-deoxy-2-fluoro-D-arabinose by a chain-extension reaction (cyanohydrin synthesis). Likewise, 4-deoxy-4-fluoro-D-glucose ° (27%) and -mannose (45%) were prepared from 3-deoxy-3-fluoro-D-arabinose. ... [Pg.183]

Introduction of F2 into 3,4,6-tri-O-acetyl-D-glucal (61) in CCI3F (Freon 11) at —78° in a manner used for the non-labeled compound (so-called cold synthesis) gave a 4 1 mixture of 3,4,6-tri-0-acetyl-2-deoxy-2-[ F]fluoro-a-D-gluco- (574) and ) -D-manno-pyranosyl fluorides (575),... [Pg.190]

Deoxy-2-[ F]fluoro-D-mannose ( F-2DFM) was prepared through treatment of 201 (see Section 11,2) with F-Bu4NF(MeCN, 75°, 30 min) or K F crown ether, as reported for the cold synthesis. F-2DFM was also prepared from methyl 4,6-di-0-acetyl-3-C>-benzoyl-2-C>-triflyl-a-D-glu-copyranoside with amino(polyether)-supported, carrier-free [ F]fluoride. [Pg.198]

Deoxy-2-[ F]fluoro-D-galactose can be prepared through an addition reaction to tri-O-acetyl-D-galactal (465), but better through Sn2 reaction (K F-Kryptofix 222 in MeCN) of methyl 3,4-0-isopropylidene-2-0-triflyl-6-0-trityl-y -D-talopyranoside (220 see Section 11,2), according to the cold synthesis. [Pg.198]

Deoxy-3-[ F]fluoro-D-glucose ( F-3DFG) was prepared - 454,467,473-476 essentially according to the procedure for the cold synthesis (see Section 11,2), namely, treatment of248 with Cs F (in DMF or HMPA), tetraalkylammonium [ F]fluoride (DMF, HMPA, or MeCN) or K F (in acetamide). 6-Deoxy-6-[ F]fluoro-a-D-galactopyranose was likewise pre-pared aceording to the cold synthesis. ... [Pg.199]

Because synthesis of l-(2-deoxy-2-fluoro-)S-D-arabinofuranosyl)cytosine (744, FAC), an elementary arabino type of nucleoside having a growth-inhibitory effect against L 1210 leukemia in mice, through direct introduction of a fluorine atom in the 2 - up (arabino) position was difficult, compound 744 was prepared by condensation of trimethylsilylated A -acetylcytosine with 3-0-acetyl-5-(7-benzoyl-2-deoxy-2-fluoro-D-arabin-ofuranosyl bromide (742), which had been prepared by periodate oxidation of 6-0-benzoyl-3-deoxy-3-fluoro-D-glucofuranose (741). Similar condensa-... [Pg.236]

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