A New Synthesis of Some 4′-Thio-D-ribonucleosides and Preliminary Enzymatic Evaluation

Synthesis and structural elucidation of 1-(3-C-ethynyl-4-thio-β-D-ribofuranosyl)cytosine (4′-thioECyd)

“…To our knowledge, only one other 4Ј-thioribonucleoside, that is, 4Ј-thioadenosine has been tested for susceptibility to bovine liver adenosine kinase, and it was revealed that this nucleoside was a poor substrate for the kinase. 16 As was the case for 4Ј-thioadenosine, the 4Ј-thiocytidine derivative, 4 was also a poor substrate for UCK. To date, potent biological activities of several 2Ј-deoxy-4Ј-thionucleoside derivatives have been reported.…”

A Facile, Alternative Synthesis of 4‘-Thioarabinonucleosides and Their Biological Activities

“…The separated water phase was concentrated under reduced pressure. The residue was purified on column chromatography over silica gel (10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20), and the anomers were separated by HPLC (YMC-PACK SIL-06 20 × 250mm, YMC Co., Ltd., Japan; 7% MeOH in CHCl3, flow rate 7 mL/min; retention time R, 23 min, , 22 min) to give R-6a (34 mg, 24%) and -6a (12 mg 5-Iodo-1-(4-thio-D-arabinofuranosyl)uracil (6c). From 11 (503 mg, 1.05 mmol), R-and -4c were obtained as described in the synthesis of 6a.…”

A Short and Efficient Synthesis of l-Thioarabinose Derivative: A Versatile Synthon for the Synthesis of l-2‘-Deoxy- 2‘,2‘-disubstituted-4‘-thionucleosides

“…A longer reaction time (>2 h) resulted in increased decomposition of the product 9 . Compound 9 was recyclized to the corresponding thiosugar 10 in 94% yield via the corresponding methanesulfonate ester in the presence of n -Bu 4 NI and BaCO 3 . Initially, we wanted to synthesize the difluoro anlogue 11 in three steps involving hydrolysis of 10 , oxidation of the resulting alcohol to the ketone, and DAST fluorination.…”

“…Despite these encouraging results and other inherent advantages, such as having a more stable glycosyl bond and increased metabolic stability, difficulties in accessing the requisite 4-thiosugars, which normally involves numerous and low-yielding steps, have prevented their development as clinical agents. Although several groups published improved syntheses of d -2‘-deoxy-4‘-thio-, d -4‘-thioribo-, and d -2‘,3‘-dideoxy-4‘-thionucleosides in the early 1990s, the synthesis of 4-thiosugars continues to be a challenge for the synthesis of 4‘-thionucleosides.…”