Thiophene ring hydroxylation: A novel application of trans-(±)-2-(phenylsulfonyl)-3-phenyloxaziridine

First Synthesis of 2,3,4-Tri-O-benzyl-5-thio-d-ribono-1,5-lactone

“…To a solution of the D-ribonic acid derivative 11 (100 mg, 0.22 mmol) in anhyd DMF (20 mL) was carefully added DIC (0.2 mL, 5 equiv) at 0 °C followed by HOBt (140 mg, 5 equiv). The solution was stirred at r.t. for 1 h. The mixture was concentrated under reduced pressure to yield a crude product, which was chromatographed on silica gel using hexanes-EtOAc (9:1) to afford 12 (72 mg, 75%) as a colourless syrup; R f 0.6 (hexanes-EtOAc, 4…”

“…In recent years a number of natural products containing a thiolactone moiety have been isolated and displayed interesting biological activities. [1][2][3][4] Some of them have shown antibiotic activity. [1][2][3][4][5] The synthesis of aldonothiolactones has been reported for only a limited number of six sulfurated cyclic compounds so far.…”

“…[1][2][3][4] Some of them have shown antibiotic activity. [1][2][3][4][5] The synthesis of aldonothiolactones has been reported for only a limited number of six sulfurated cyclic compounds so far. For example, per-O-alkylated derivatives of 5-thio-D-glucono-1,5-lactone 6 and per-O-benzylated 5-thio-D-xylono-1,5-lactone 7 were obtained by OH-1 oxidation of the corresponding per-Oalkylated 5-thio-D-glycopyranose derivatives.…”