A practical synthesis of 2-deoxy-2-fluoro-d-arabinofuranose derivatives

Structural Requirements for the Enzymatic Deamination of Cytosine Nucleosides

“…Introduction of methyl substituent on C ( 6 ) significantly reduces the susceptibility of the ribo-or arabinocytosine nucleoside to deamination by the enzyme. 0.05 2'-Fluoro-ara-C [36] 0.40 2'-Fluoro-ara-5-fluoro-Cd) 2.45 2'-Chloro-ara-C [37] 0.05 2'-Bromo-ara-Ce) < 0.05 2'-Mesyloxy-ara-Ce) < 0.05 ") High blank. Of the parent 1-P-D-pentofuranosylcytosines, cytidine is the best substrate for the mouse kidney deaminase followed in decreasing order by 2'-deoxycytidine, ara-C, xylo-C and lyxo-C.…”

Synthesis of [18F]‐labeled 2′‐deoxy‐2′‐fluoro‐5‐methyl‐1‐β‐D‐arabinofuranosyluracil ([18F]‐FMAU)

“…3,4 However, the incorporation of fluorine in the arabino configuration at C-2 of the sugar followed by coupling with the pyrimidine base has been successful towards the syntheses of these nucleosides. [3][4][5][6] The conventional methods for the stereospecific (arabino) incorporation of fluorine involve use of KHF 2 or Et 3 N Á 3HF in excess (6 equiv) as the fluorinating agent and require long reaction times (6 h).…”

“…7 Coupling of the sugar with a pyrimidine base often involves conversion of the protected sugar to its 1-bromo-derivative, which is then treated with a protected pyrimidine over a lengthy period of time ranging from 16 h to 7 days. [3][4][5][6] As in the case of the fluorination reaction discussed above these conditions are not appropriate for a synthesis using a reactant labeled with short half-life isotopes such as 18 F. Another method of coupling the glycosyl moiety to the pyrimidine base used a Friedel-Crafts catalyst and a 2-substituted ribofuranose to produce exclusively the b-anomer of the nucleoside. 8 Very limited work has been done on pyrimidine glycosylation with protected 2-deoxyarabinose.…”

Synthesis of 2′-Deoxy-2′-[18F]Fluoro-9-β-D-Arabinofuranosylguanine: a Novel Agent for Imaging T-Cell Activation with PET

“…There are many reports on the indirect synthesis of 2′-deoxy-2′-fluoro-9-β-D-arabinofuranosylguanine (F-AraG) in which fluorine is first introduced in the arabino position at C-2, and then fluorinated sugar reacted with the purine base [22][23][24]. [25].…”