Hydrogen Peroxide → 3'-Deoxy-3'-(3-hydroxypropyl)-5'-O-tert-butyldiphenylsilylthymidine

Participants

Reaction Steps

Compound 37 (0.74 g, 2 mmol) was treated with BH3Me2S (0.388 g, 5.12 mmol) in THF (10 ml). The reaction mixture was quenched with MeOH (0.7 mL). H2O (3 mL) and NaHCO3 (1.11 g, 13.3 mmol) were added to the reaction mixture followed by H2O2 (30%, 1.91 mL, 16.92 mmol). After work-up, the residue was purified by silica gel chromatography. The product was crystallized from ether/hexane to furnish 0.41 g of the product as white needles. mp 150-151° C.

Provenance & Evidence